PubMed · 4248513
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L Goldman. 1970. Griseofulvin.. https://pubmed.ncbi.nlm.nih.gov/4248513/
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Enzymatic hydrogenation of 2'-demethoxy-2'-methyldehydrogriseofulvin (5) with a cell-free system of Streptomyces cinereocrocatus afforded (+)-2'-demethoxy-2'-methylgriseofulvin (6). The structure of 6 was determined on the basis of comparisons of the proton nuclear magnetic resonance spectrum, mass spectrum, and circular dichroism with those of a standard specimen which was synthesized chemically. The results demonstrated that when the 2'-position of (-)-dehydrogriseofulvin was substituted with a methyl group, its hydrogenation with the cell-free system occurred stereoselectively at the 5',6'-position.
In order to elucidate the structure-activity relationship of griseofulvin (1), (+/-)-6-demethyl analog (3), 2-demethoxy-6-demethyldihydro analog (4), (+/-)-dechloro-6-ethyl analog (5), (+/-)-dechloro-6-epi-ethyl analog (6), (+/-)6-ethyl analog (7) and (+/-)-6-epi-ethyl analog (8) were synthesized by a Diels-Alder cycloaddition of alkylidene ketones (16, 17 18, 19 and 20) with modified 1,3-butadienes (21 or 22). Their biological activities were examined against fungi.