Tetrahedron p. 12523 - 12538 (1998)
Update date:2022-08-04
Topics:
Gao, Yang
Wu, Wen-Lian
Wu, Yu-Lin
Ye, Bin
Zhou, Rong
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 unsaturated aldehyde to provide the diol 5. Diol 5 could also be obtained from 5-(3-acetoxypropyl)-2-furaldehyde or 5-(4- acetoxybutyl)-2-furaldehyde and alkynyllithium. By careful treatment of 5 or 7 with acid, dehydration-cyclization occurred to give the desired spiroketal- enol ether in moderate to excellent yields.
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Doi:10.1021/ja9740069
(1998)Doi:10.1211/146080899128734604
(1999)Doi:10.1021/om980597f
(1998)Doi:10.1021/ic9809153
(1998)Doi:10.1007/BF02495717
(1998)Doi:10.1016/S0223-5234(98)80042-1
(1998)