Total synthesis of (1RS, 4SR, 5RS)-4-(5-hydroxy-4, 8-dimethyl-7-nonen-1-yl)-4-methyl-3, 8-dioxabicyclo [3.2. 1] octane-1-acetic acid from geraniol

…, MP Wachter, HM Werblood, RE Adams

文献索引：Hajos, Zoltan G.; Wachter, Michael P.; Werblood, Harvey M.; Adams, Richard E. Journal of Organic Chemistry, 1984 , vol. 49, # 14 p. 2600 - 2608

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被引用次数: 14

摘要

(E)-Geraniol (4) has been converted via 13 steps involving epoxidations, hydrolytic epoxide ring opening, and two ring cloeurea to the key intermediate 3, 8dioxabicyclo [3.2. l] octane alcohol 10 having stereochemical integrity at all three centers of asymmetry. Extension of the threecarbon side chain of 10 and attachment of the acetic acid side chain at C-1 in nine steps completed the geraniol-based total synthesis of the zoapatanol related bicyclic acid ...