Seven-membered rings via silyl enol ether participation in the olefin cyclization. Anti-Markownikoff cyclization in biomimetic terpene synthesis

S Hashimoto, A Itoh, Y Kitagawa…

Index: Hashimoto,S. et al. Journal of the American Chemical Society, 1977 , vol. 99, # 12 p. 4192 - 4194

Full Text: HTML

Citation Number: 44

Abstract

(1) of karahanaenone,'humulene, 2 and lanosterol (C ring) 3 are the most notable examples, it is surprising that there seems to be no appropriate chemical precedent for such processes. We have been intrigued for some time in the possibility of terminating cationic cyclization via nucleophilic participation of silyl enol ether which, if successful, would result in the formation of several cyclic terpenes otherwise directly~ nattainable.~ The present communication ...