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

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journal contribution
posted on 17.09.2010, 00:00 by David M. Hodgson, Tanzeel Arif
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 (6S,7R,Z)-7-hydroxy-2-((E)-6-hydroxy-4-methylhex-4-enylidene)-6,10-dimethylundec-9-enyl acetate (12).