31 (+)-および(-)-2'-DemethoxydehydrogriseofulvinのStreptomyces cinereocrocatusによる微生物変換の立体化学
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The stereochemistry of microbial transformation of the titled compounds was elucidated by 400MHz PMR and 41.41 MHz ^2H-NMR and by CD spectral data. Streptomyces cinereocrocatus was used as a micro-organismus with the intention of comparing the results with those obtained previously on (-)- and (+)-dehydrogriseofulvin and their analogs (Chart 1). (+)- and (-)-2'-Demethoxydehydrogriseofulvin (5 and 6) synthesized as substrates were subjected to the microbial transformation by S. cinereocrocatus. The transformation of (-)-enantiomer afforded (+)-2'-demethoxy-2',3'-dihydrodehydrogriseofulvin (16) as a sole product in 60% yield. On the other hand, the microbial transformation of (+)-enantiomer gave (+)-2'-demethoxygriseofulvin and a mixture of (-)- and (+)-2'-demethoxy-2',3'-dihydrodehydrogriseofulvin (13 and 16) in 12 and 8% yields, respectively. The results indicate that the microbial transformations take place directly and/or after isomerization with hydrogenation depending on (+)- or (-)-2'-demethoxydehydrogriseofulvin (Chart 4). In order to elucidate the stereochemistry of the microbial hydrogenation, deuterated substrates (5a,5b, 6a and 6b) were subjected to the same microbial transformation as performed in undeuterated substrates, and undeuterated stubstrates, on the other hand, were transformed in a medium containing deuterium oxide. PMR and ^2H-NMR analyses (Fig. 2 and 3) of the deuterated products revealed that hydrogenations of the dienones proceed in transdiaxial manner to give the corresponding products in the results so far obtained (Chart 5 and 6).
- 天然有機化合物討論会の論文
- 1982-09-10
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