A straightforward synthetic approach to the spiroketal-enol ethers synthesis of natural antifeeding compound tonghaosu and its analogs

Y Gao, WL Wu, YL Wu, B Ye, R Zhou

Index: Gao, Yang; Wu, Wen-Lian; Wu, Yu-Lin; Ye, Bin; Zhou, Rong Tetrahedron, 1998 , vol. 54, # 41 p. 12523 - 12538

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Citation Number: 39

Abstract

Tonghaosu 1, a natural product discovered from several plants of tribe Athemdeae, is a [4.4] spiroketal with an enediyne side-chain and shows interesting insect antifeeding activity. In this paper a general and convenient synthetic methodology for the synthesis of 1, 2 and its spiroketal-enol ether derivatives is described. Thus, 3-(2′-furyl)-propan-1-ol 7a or 4-(2′- furyl)-butan-1-ol 7b prepared from furaldehyde was treated with n-butyl lithium and ...