General method of synthesis of cyclopentanoid terpenic acids. Stereocontrolled total syntheses of (.+-.)-isocomenic acid and (.+-.)-epiisocomenic acid

…, JM Revol, BC Ranu, T Hudlicky

Index: Short, Robert P.; Revol, Jean-Marc; Ranu, B. C.; Hudlicky, Tomas Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4453 - 4461

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Citation Number: 38

Abstract

13. The internal cyclopropanation of exocyclic acrylates and the subsequent vinylcyclopropane-cyclopentene rearrangement were used in an efficient synthesis of a key intermediate, triquinane 23, containing all of the contiguous quaternary centers. The utilization of abnormal Reformatsky reaction of 4-bromocrotonates with keto esters served in the preparation of important precursors to the cyclopentene annulation sequence, the ...