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Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
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no DOI — not checkedQuenching with methyl sulfide proved most practical when cleaving large numbers of compounds simultaneously since the reagent can be conveniently added as a THF solution to all reaction vessels. After 10 min the resin can be removed and the filtrate concentrated directly to provide the desired benzopyran cleavage product. Given the volatility of methyl sulfide, any excess was removed during evaporation leaving only the desired cleavage product and a trace amount of DMSO (produced by oxidation of Me2S). This residual DMSO is inconsequential since most samples are directly dissolved in DMSO for biological screening. As described in the following paper, it is this facile cleaving operation which greatly facilitated the use of automation in synthesizing the 10 000-membered library.25Incidentally, for individual cleavages of larger amounts of resin, one can also employ a standard aqueous workup using sodium sulfite to quench the residual oxidant (see Experimental Procedures in the Supporting Information for the details of both protocols).
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