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Convergent synthesis of trisubstituted Z-allylic esters by Wittig-Schlosser reaction.

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 (6S,7R,Z)-7-hydroxy-2-((E)-6-hydroxy-4-methylhex-4-enylidene)-6,10-dimethylundec-9-enyl acetate (12).
Publication status:
Published

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Publisher copy:
10.1021/ol101843q

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic letters
Volume:
12
Issue:
18
Pages:
4204-4207
Publication date:
2010-09-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:4fa76bea-11e2-4421-a449-6d8cdf06962f
Source identifiers:
67473
Local pid:
pubs:67473
Language:
English

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