Synthesis of rac-hippospongic acid A and revision of the structure

M Tokumasu, H Ando, Y Hiraga, S Kojima…

Index: Tokumasu, Munetaka; Ando, Hiroshi; Hiraga, Yoshikazu; Kojima, Satoshi; Ohkata, Katsuo Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 4 p. 489 - 496

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Citation Number: 22

Abstract

rac-Hippospongic acid A of the reported structure 1 and the revised structure 2 were synthesized. The synthetic strategy of these compounds consists of homologation of (2E, 6E, 10E)-geranylgeraniol and (2E, 6E)-farnesol, respectively, Wadsworth–Emmons reaction, and cyclization to form the tetrahydropyran ring bearing an α-methylene group on the carboxylic moiety. Spectral comparisons of the synthetic compounds 1, 2 and the natural ...