Microbiologically modified chiral synthon. III. 4,9-Dimethyl-3,5-dioxo-Δ(4(10))-octalin for formal total syntheses of certain sesquiterpenoids

DOI: 10.1248/cpb.39.2973

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2973 - 2979 (1991)

Update date:2022-09-26

Topics:

Authors:

Shimizu Shimizu

Ohkura Ohkura

Akita Akita

Oishi Oishi

Iitaka Iitaka

Inayama Inayama

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Article abstract of DOI:10.1248/cpb.39.2973

Microbiological enantioselective transformation of 4,9-dimethyl-3,5-dioxo-Δ(4(10))-octalin, (±)-1 was accomplished with various yeasts, e.g. Rhodotorula ruhra. With properly selected microorganisms, (±)-4,9S-dimethyl-5S-hydroxy(2a) and (-)-4,9R-dimethyl-5S-hydroxy-3-oxo-Δ(4(10))-octalin (3b), (-)-4,9R-dimethyl-3S-hydroxy- (6b) and (±)4,9S-dimethyl-3S-hydroxy-5-oxo-Δ(4(10))-octalin (7a) were obtained with high optical purity. These compounds have now become available for the total syntheses of sesquiterpenoids such as tuberiferine and temisin.

Full text of DOI:10.1248/cpb.39.2973

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