Model studies of the biosynthesis of non-head-to-tail terpenes. Rearrangements of the chrysanthemyl system

CD Poulter, LL Marsh, JM Hughes…

Index: Poulter,C.D. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 3816 - 3823

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Citation Number: 40

Abstract

Abstract: A study of the solvolysis reactions of the chrysanthemyl system is reported. In water the chrysanthemyl cation (2) gives the naturally occurring monoterpene alcohols chrysanthemol (1-OH), artemisia alcohol (3-OH), yomogi alcohol (1 1-OH), and santolina alcohol (5-OH). Rupture of the C (1')-C (3') cyclopropane bond of 2 gives an isomeric allylic cation which reacts with solvent to yield artemisia alcohol (3-OH) and yomogi alcohol (1 1- ...