Stereoselective total syntheses of (.+-.)-gymnomitrol and (.+-.)-gymnomitrene

SC Welch, S Chayabunjonglerd…

文献索引：Welch, Steven C.; Chayabunjonglerd, Suthep; Rao, A.S.C.Prakasa Journal of Organic Chemistry, 1980 , vol. 45, # 21 p. 4086 - 4093

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被引用次数: 28

摘要

Stereoselective total syntheses of (&)-gymnomitrol (2A) and (f)-gymnomitrene (2B) in 12 synthetic stages each from 2-methylcyclopentanone (3) are presented. The key features of these syntheses are (a) the conjugate addition of lithium dimethylcopper to enone 8 followed by alkylation of the intermediate enolate anion with allyl chloride to afford ketone 9,(b) stereoselective alkylation of ketone 9,(c) a modified intramolecular Claisen condensatilm ...