Microbial stereodifferentiating reduction of (.+-.)-4-methyl-and (.+-.)-6-methyl-1-oxo [2.2] metacyclophanes and revision of the absolute configuration of 4-substituted [ …

M Nakazaki, Y Hirose, T Shimizu, T Suzuki…

Index: Nakazaki, Masao; Hirose, Yoshiki; Shimizu, Toru; Suzuki, Takaaki; Ishii, Akira; Makimura, Masaru Journal of Organic Chemistry, 1980 , vol. 45, # 8 p. 1428 - 1435

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Citation Number: 7

Abstract

Partial oxidative hydrolysis of 4-bromo-1, 1, 10, 10-bis (trimethylenedithio)[2.2 lmetacyclophane (7) yielded the bromo ketones 8 and 9 which were respectively converted into (*)-4-methyl-(3) and (*)-6-methyl-l-oxo [2.2]-metacyclophanes (4). The unambiguous synthesis of (*)-3 from 2, 5-dimethylbenzoic acid (18) assigned their structures. Incubation of (&)-3 with Rhodotorula rubra gave a mixture of (-)-ketone 3,(-) axial alcohol 38, and (-) ...