Tetrahedron letters

An efficient synthesis of the CD rings model for merrilactone A

K Harada, H Ito, H Hioki, Y Fukuyama

Index: Harada, Kenichi; Ito, Hitoshi; Hioki, Hideaki; Fukuyama, Yoshiyasu Tetrahedron Letters, 2007 , vol. 48, # 35 p. 6105 - 6108

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Citation Number: 13

Abstract

A synthetic route to the CD rings of merrilactone A was explored by using the model system 9a, which was easily converted from 7, 7-dibromohepta-2, 6-dienoic acid ethyl ester (8) by the successive Stille–Mizoroki–Heck reaction. The D ring 14 was constructed by applying the intramolecular Tsuji–Trost reaction to the formation of a γ-lactone, whereas the formation of the C ring 18 was effectively accomplished in one step by methylation and conjugate ...