Organic letters

Convergent Synthesis of Trisubstituted Z-Allylic Esters by Wittig− Schlosser Reaction

DM Hodgson, T Arif

Index: Hodgson, David M.; Arif, Tanzeel Organic Letters, 2010 , vol. 12, # 18 p. 4204 - 4207

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Citation Number: 17

Abstract

β-Lithiooxyphosphonium ylides, generated in situ from aldehydes and Wittig reagents, react readily with halomethyl esters to form trisubstituted Z-allylic esters. The methodology was applied to a total synthesis of the geranylgeraniol-derived diterpene (6 S, 7 R, Z)-7-hydroxy- 2-((E)-6-hydroxy-4-methylhex-4-enylidene)-6, 10-dimethylundec-9-enyl acetate (12).

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