MICROBIOLOGICALLY MODIFIED 4, 9-DIMETHYL-Δ4 (10) -OCTAL-3, 7-DIONES AS THE CHIRAL SYNTHON FOR FORMAL TOTAL SYNTHESES OF C (8) OXYGENATED SESQUITERPENOIDS

Seiichi Inayama; Nobuko Shimizu; Tamiko Ohkura; Hiroyuki Akita; Takeshi Oishi; Yoichi Iitaka

doi:10.1248/cpb.35.429

MICROBIOLOGICALLY MODIFIED 4, 9-DIMETHYL-Δ⁴ (10) -OCTAL-3, 7-DIONES AS THE CHIRAL SYNTHON FOR FORMAL TOTAL SYNTHESES OF C (8) OXYGENATED SESQUITERPENOIDS

Seiichi Inayama, Nobuko Shimizu, Tamiko Ohkura, Hiroyuki Akita, Takeshi Oishi, Yoichi Iitaka

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Keywords: asymmetric induction, microbiological reduction, 3, 7-octaldione, (7S) -hydroxyoctal-3-one, yeast, Rhodotorula rubla, chiral synthon, sesquiterpenoids, (-) -artemisin, (+) -isotelekin

JOURNAL FREE ACCESS

1987 Volume 35 Issue 1 Pages 429-432

DOI https://doi.org/10.1248/cpb.35.429

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Abstract

4, (9S) - (2a) and 4, (9R) -dimethyl- (7S) -hydroxy-Δ⁴⁽¹⁰⁾ -octal-3-one (2b) were prepared in high optical purity (>99% ee) and in moderate yield by asymmetric reduction of the corresponding racemic diketone (lab) using yeasts. These compounds were used for the formal total synthesis of C (8) oxygenated sesquiterpenoids such as (-) -artemisin, (-) -yomogin, (-) -3-oxodiplophyllin, β-elemenone, (+) -isotelekin and (+) -cuauhtemone.

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