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Bioactive marine metabolites. 48. Cinachyrolide A: a potent cytotoxic macrolide possessing two spiro ketals from marine sponge Cinachyra sp

https://doi.org/10.1021/ja00063a017
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Intricate aspects of sponge chemistry
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Totalsynthese von Altohyrtin A (Spongistatin 1): Teil 1
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Spongistatine, Cynachyrolide oder Altohyrtine? Marine Makrolide in der Krebsforschung
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The Spongistatins: Architecturally Complex Natural Products—Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment
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Stereocontrolled Total Synthesis of (+)‐Altohyrtin A/Spongistatin 1
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The Spongistatins: Architecturally Complex Natural Products-Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment
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Stereocontrolled Total Synthesis of (+)-Altohyrtin A/Spongistatin 1 Financial support was provided by the EPSRC (GR/L41646), Cambridge Commonwealth Trust (Scholarship to M.J.C.), EC (Marie Curie Postdoctoral Fellowship to J.L.A.), DFG (Postdoctoral Fellowship to T.T.), NSERC-Canada (Postdoctoral…
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Coupling Constants Determined by ECOSY
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Ether Transfer Methodology: Application to the Synthesis of Polyketide Natural Products
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Application of The [4+3] Cycloaddition Reaction To The Synthesis of Natural Products
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Multicomponent Reactions in Natural Product Synthesis
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Porifera (Sponges)–2
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Enantioselektive Synthese von Altohyrtin C (Spongistatin 2): Synthese der AB‐ und CD‐Spiroketale
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Enantioselektive Synthese von Altohyrtin C (Spongistatin 2): Synthese des EF‐Bis‐(tetrahydropyran)‐Fragments
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Total Synthesis of Spongistatin 1: A Synthetic Strategy Exploiting Its Latent Pseudo‐Symmetry
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Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the AB‐ and CD‐Spiroketal Subunits
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Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the EF‐Bis(pyran) Subunit
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Total Synthesis of Spongistatin 1: A Synthetic Strategy Exploiting Its Latent Pseudo‐Symmetry
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Natural‐Product Diversity of the New Caledonian Marine Ecosystem Compared to Other Ecosystems: A Pharmacologically Oriented View
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Short Diastereoselective Synthesis of the C1–C13 (AB Spiroacetal) and C17–C28 Fragments (CD Spiroacetal) of Spongistatin 1 and 2 through Double Chain‐Elongation Reactions
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PdII‐Catalyzed Spiroketalization of Ketoallylic Diols
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ChemInform Abstract: Bioactive Marine Metabolites. Part 48. Cinachyrolide A (I): A Potent Cytotoxic Macrolide Possessing Two Spiro Ketals from Marine Sponge Cinachyra sp.
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The Medicinal Potential of Promising Marine Macrolides with Anticancer Activity
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Spirangien A and B, Highly Cytotoxic and Antifungal Spiroketals from the Myxobacterium Sorangium cellulosum: Isolation, Structure Elucidation and Chemical Modifications
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Synthetic Studies toward the CD Spiroketal of Spongistatins
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Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides
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Synthesis of Cytotoxic Marine Macrolides: An Aldol-Based Approach to Spongistatin 1 (Altohyrtin A)
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C
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Isolation of Marine Natural Products
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Screening of the Antarctic marine sponges (Porifera) as a source of bioactive compounds
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Absolute stereostructures of altohyrtin A and its congeners, potent cytotoxic macrolides from the Okinawan marine sponge hyrtios altum
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Reversible covalent attachment of C60 to a furan-functionalized resin
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Regioselective and stereoselective reductive cleavage of 1,7-dioxaspiro[5.5]undecane alcohols
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Studies in marine macrolide synthesis: Stereocontrolled synthesis of the AB-spiroacetal subunit of spongistatin 1 (altohyrtin A)
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Correlations Through Space: The Nuclear Overhauser Effect
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Discovery of New Macrolides from Marine Organisms
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Spongistatins: Biological activity and synthetic studies
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Dictyoceratidan poisons: Defined mark on microtubule-tubulin dynamics
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Synthesis and biological evaluation of analogs of altohyrtin C (spongistatin 2)
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Spongipyran synthetic studies. Total synthesis of (+)-spongistatin 2
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Spongipyran synthetic studies. Evolution of a scalable total synthesis of (+)-spongistatin 1
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Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B
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Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals
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Formal total synthesis of altohyrtin C (spongistatin 2). Part 2: Construction of fully elaborated ABCD and EF fragments
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Cinachyramine, the novel alkaloid possessing a hydrazone and two aminals from Cinachyrella sp.
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Asymmetric Epoxide Cyclisation Route to the F-pyran Fragment of the Altohyrtins and Key Aldol Studies
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Molecular modeling of 5-desacetylaltohyrtin A, a spongean cytotoxic macrolide
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Reidispongiolide A and B, two new potent cytotoxic macrolides from the new caledonian sponge Reidispongia coerulea
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8-oxabicyclo[3.2.1]oct-6-en-3-one as a module for the synthesis of β-alkoxy-δ-valerolactones relevant to natural products and drugs
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Enantioselective total synthesis of altohyrtin C (spongistatin 2)
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Asymmetric synthesis of polyacetate derived building blocks with α-oxyanion functionality. Lewis acid catalyzed opening of 2,9-dioxabicyclo[3.3.1]nonan-3-ones
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Synthetic studies on spongistatins: synthesis of the C29–C44 fragment
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Approaches to the C-24 to C-37 perimeter of altohyrtin A
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Addition of metalated pyrones to β-alkoxy aldehydes: Synthesis of hydroxylated spiroketals
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In situ alcohol oxidation-Wittig reactions
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A novel route to monoanomeric spiroketals
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Stereocontrolled synthesis of the CD subunit of the marine macrolide altohyrtin A
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A novel macrodiolide synthesis using the Mn(III)-based radical cyclization of terminal alkadienes and oligomethylene di(3-oxobutanoate)s
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Chapter Three 3-Alkylpiperidine alkaloids isolated from marine sponges in the order haplosclerida
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Synthesis of the C29–C37 segment of spongistatin 1
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Synthesis and biological evaluation of a spongistatin AB-spiroketal analogue
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Synthesis and in vitro cancer cell growth inhibitory activity of monocyclic model compounds containing spongistatin triene side-chains
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Correlations through space: The nuclear Overhauser effect
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Chapter 8 Correlations through space: The nuclear overhauser effect
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Biological activities of natural halogen compounds
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Bioactive marine macrolides
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Total Synthesis of Spongistatin 1 (Altohyrtin A): A Tale of Ten Aldols
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Sexual reproduction of the potentially cultivable sponge Mycale phyllophila (Porifera, Demospongiae)
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Structural Simplification of Natural Products
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Advances in the Total Synthesis of Biologically Important Marine Macrolides
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Nonanomeric Spiroketals in Natural Products: Structures, Sources, and Synthetic Strategies
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Asymmetric Total Synthesis of Spongistatins 1 and 2
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A Second-Generation Synthesis of the C1−C28 Portion of the Altohyrtins (Spongistatins)
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Spirastrellolide A, An Antimitotic Macrolide Isolated from the Caribbean Marine Sponge Spirastrella coccinea
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Racemization in Prins Cyclization Reactions
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Design, Synthesis, and Biological Evaluation of Diminutive Forms of (+)-Spongistatin 1: Lessons Learned
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Callipeltoside A: A Cytotoxic Aminodeoxy Sugar-Containing Macrolide of a New Type from the Marine Lithistida Sponge Callipelta sp.
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A General Synthetic Entry to Strychnos Alkaloids of the Curan Type via a Common 3a-(2-Nitrophenyl)hexahydroindol-4-one Intermediate. Total Syntheses of (±)- and (−)-Tubifolidine, (±)-Akuammicine, (±)-19,20-Dihydroakuammicine, (±)-Norfluorocurarine, (±)-Echitamidine, and (±)-20-Epilochneridine1
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Synthesis of the C29−C44 Portion of Spongistatin 1 (Altohyrtin A)
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Long-Chain 2H-Azirines with Heterogeneous Terminal Halogenation from the Marine Sponge Dysidea fragilis
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Total Synthesis of the Strychnos Alkaloids (±)-Akuammicine and (±)-Norfluorocurarine from 3a-(o-Nitrophenyl)hexahydroindol-4-ones by Nickel(0)-Promoted Double Cyclization
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A Method for Constructing the C2−C12 Dispiroacetal Moiety of Altohyrtin A
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A Method for Constructing the C18−C28 Dispiroacetal Moiety of Altohyrtin A
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Synthesis of the C1−C28 Portion of Spongistatin 1 (Altohyrtin A)
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Bidirectional Asymmetric Allylboration. A Convenient Asymmetric Synthesis of C2-Symmetric 3-Methylenepentane-1,5-diols and Rapid Access to C2-Symmetric Spiroketals
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Tetillapyrone and Nortetillapyrone, Two Unusual Hydroxypyran-2-ones from the Marine Sponge Tetilla japonica
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A Modular Approach to Marine Macrolide Construction. 3. Enantioselective Synthesis of the C1−C28 Sector of Spongistatin 1 (Altohyrtin A)
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Synthesis of the C16−C28 Spiroketal Subunit of Spongistatin 1 (Altohyrtin A): The Pyrone Approach
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An Aldol Approach to the Synthesis of the EF Fragment of Spongistatin 1
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Spongistatin Synthetic Studies. An Efficient, Second-Generation Construction of an Advanced ABCD Intermediate
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Diastereoselective Synthesis of the C(17)−C(28) Fragment (The C−D Spiroketal Unit) of Spongistatin 1 (Altohyrtin A) via a Kinetically Controlled Iodo-Spiroketalization Reaction
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Synthesis of the C(2)−C(13) Fragment (The A−B Spiroketal Unit) of Spongistatin 1 (Altohyrtin A): Use of a Common Intermediate for the Synthesis of Both Spongistatin Spiroketals
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Total Synthesis of (+)-Spongistatin 1. An Effective Second-Generation Construction of an Advanced EF Wittig Salt, Fragment Union, and Final Elaboration
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A Practical and Efficient Synthesis of the C-16−C-28 Spiroketal Fragment (CD) of the Spongistatins
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Spongistatin Synthetic Studies. Evolution of a Scalable Synthesis for the EF Fragment of (+)-Spongistatin 1 Exploiting a Petasis−Ferrier Union/Rearrangement Tactic
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Enantio- and Diastereoselective Allylmetalations: An Easy and Efficient Access to the AB Spiroketal of Spongistatin
inferred← citeshttps://doi.org/10.1021/ol063083iopenalex-snapshot
A Modular Approach to Marine Macrolide Construction. 4. Assembly of C36−C51 and C29−C44 Building Blocks and Evaluation of Key Coupling Reactions Targeting Spongistatin 1 (Altohyrtin A)
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The Solution Structure of (+)-Spongistatin 1 in DMSO
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Design, Synthesis, and Biological Evaluation of EF- and ABEF- Analogues of (+)-Spongistatin 1
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Stereoselective Synthesis of Substituted Tetrahydropyrans via Domino Olefin Cross-Metathesis/Intramolecular Oxa-Conjugate Cyclization
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Exploiting Pseudo C2-Symmetry for an Efficient Synthesis of the F-Ring of the Spongistatins
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New Efficient Route to an Advanced Precursor of the AB Spiroketal of Spongistatins
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Gram-Scale Synthesis of (+)-Spongistatin 1: Development of An Improved, Scalable Synthesis of the F-Ring Subunit, Fragment Union, and Final Elaboration
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A Method for Constructing the C44−C51 Side Chain of Altohyrtin C
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Direct and highly regioselective and enantioselective allylation of β-diketones
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Design and 22-step synthesis of highly potent D-ring modified and linker-equipped analogs of spongistatin 1
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Macromarines: A Selective Account of the Potential of Marine Sponges, Molluscs, Soft Corals and Tunicates as a Source of Therapeutically Important Molecular Structures
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Synthesis and biological evaluation of spongistatin/altohyrtin analogues: E-ring dehydration and C46 side-chain truncationElectronic supplementary information (ESI) available: spectroscopic data for compounds 2 and 3. See http://www.rsc.org/suppdata/cc/b2/b212651f/
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The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment
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Azeotropic reflux chromatography: an efficient solution to a difficult separation in the scale-up synthesis of spongistatin 1
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Complex fragment coupling by crotylation: a powerful tool for polyketide natural product synthesis
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Amphidinolide N, a novel 26-membered macrolide with remarkably potent cytotoxicity from the cultured marine dinoflagellate Amphidinium sp.
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Antineoplastic agents 300. Isolation and structure of the rare human cancer inhibitory macrocyclic lactones spongistatins 8 and 9
inferred← citeshttps://doi.org/10.1039/c3sc22186eopenalex-snapshot
Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts
inferred← citeshttps://doi.org/10.1039/c3sc50304fopenalex-snapshot
Synthesis of spongistatin 2 employing a new route to the EF fragment
inferred← citeshttps://doi.org/10.1039/c5np00014aopenalex-snapshot
Conformation–activity relationships of polyketide natural products
inferred← citeshttps://doi.org/10.1039/c8cs00532jopenalex-snapshot
Application of (4+3) cycloaddition strategies in the synthesis of natural products
inferred← citeshttps://doi.org/10.1039/co9940100259openalex-snapshot
Synthetic developments in host–guest chemistry
inferred← citeshttps://doi.org/10.1039/co9970400061openalex-snapshot
Synthetic developments in host–guest chemistry
inferred← citeshttps://doi.org/10.1039/d1cc00442eopenalex-snapshot
Conquering peaks and illuminating depths: developing stereocontrolled organic reactions to unlock nature's macrolide treasure trove
inferred← citeshttps://doi.org/10.1051/medsci/20143003021openalex-snapshot
Recherche de substances naturelles à activité thérapeutique (2)
inferred← citeshttps://doi.org/10.1080/10286020802030892openalex-snapshot
New ceramides from the sponge Cinachyra cavernosa
inferred← citeshttps://doi.org/10.1097/jbr.0000000000000143openalex-snapshot
Natural therapeutics for cancer treatment: success, challenges, and prospect
inferred← citeshttps://doi.org/10.1128/9781555817770.ch18openalex-snapshot
Microbes from Marine Sponges: A Treasure Trove of Biodiversity for Natural Products Discovery
inferred← citeshttps://doi.org/10.1135/cccc2008181openalex-snapshot
Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of Spongistatin 1 (Altohyrtin A)
inferred← citeshttps://doi.org/10.1201/b19081-17openalex-snapshot
Medicinal Chemistry and Lead Optimization of Marine Natural Products
inferred← citeshttps://doi.org/10.1264/jsme2.me11270openalex-snapshot
Actinobacteria Associated with the Marine Sponges Cinachyra sp., Petrosia sp., and Ulosa sp. and Their Culturability
inferred← citeshttps://doi.org/10.2174/187152009787313800openalex-snapshot
Marine Macrolides, a Promising Source of Antitumor Compounds
inferred← citeshttps://doi.org/10.2331/fishsci.68.sup2_1583openalex-snapshot
Bioactive marine natural products research
inferred← citeshttps://doi.org/10.3109/15569549609064082openalex-snapshot
Bioactive Substances from Marine Sponges
inferred← citeshttps://doi.org/10.3390/ijms242417584openalex-snapshot
Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications
inferred← citeshttps://doi.org/10.3390/md14080139openalex-snapshot
The Role of Spongia sp. in the Discovery of Marine Lead Compounds
inferred← citeshttps://doi.org/10.70675/c97ea6c4zc6b1z4904z992cza9a1bb4c8899openalex-snapshot
Développement de nouvelles réactions radicalaires sans étain en glycochimie : élaboration de spirocétals et débenzylations régiosélectives
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