Elsevier

Tetrahedron Letters

Volume 48, Issue 8, 19 February 2007, Pages 1429-1433
Tetrahedron Letters

Synthesis of moenocinol and its analogs using BT-sulfone in Julia-Kocienski olefination

https://doi.org/10.1016/j.tetlet.2006.12.119Get rights and content

Abstract

Moenocinol (C25H42O), the acyclic terpenoid unsaturated lipid part of moenomycin antibiotics, was prepared by an expedient method, which comprised organometallic reaction, Julia-Kocienski olefination, and enolate carbon bond formation as the key steps. The starting materials, nerol and 3-butyn-1-ol, were elaborated to the benzothiazole sulfone 2 and aldehyde 3, and the subsequent Julia-Kocienski olefination occurred in a stereospecific manner to give the desired 6E-configuration of moenocinol. Moenocinol (1) was thus synthesized by 10 linear steps in 12% overall yield, and its analogs 23, 24, and 28 with different chain lengths and unsaturation degrees were also realized by the similar reaction sequences.

Graphical abstract

The lipid part of moenomycin antibiotics, moenocinol (C25H42O), was synthesized by 10 linear steps in 12% overall yield.

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Acknowledgments

We thank Academia Sinica for financial support and Professor Jim-Min Fang (Department of Chemistry, National Taiwan University) for helpful discussion.

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