Highly stereoselective total synthesis of methynolide, the aglycon of the 12-membered macrolide antibiotic methymycin. I. Synthesis of a prelog-djerassi lactone-type …

Y OIKAWA, T TANAKA, K HORITA, I NODA…

文献索引：Oikawa; Tanaka; Horita; et al. Chemical and Pharmaceutical Bulletin, 1987 ,  vol. 35,  # 6  p. 2184 - 2195

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被引用次数: 21

摘要

For the highly stereoselective synthesis of methynolide (2), the aglycon of the 12-membered macrolide antibiotic methymycin (1), a Prelog-Djerassi lactone-type chiral intermediate (7a) bearing four chiral centers corresponding to the C-2, C-3, C-4, and C-6 positions was synthesized from D-glucose. In this synthesis, several stereocontrolled reactions such as hydroboration, catalytic hydrogenation, etc. were successfully applied. The utility of the 4- ...