A highly catalytic asymmetric conjugate addition: Synthesis of the C14-C20 fragment of antibiotic TMC-151A, siphonarienal and siphonarienone

Tze Keong Lum; Shun Yi Wang; Teck Peng Loh

doi:10.1021/ol702715q

A highly catalytic asymmetric conjugate addition: Synthesis of the C14-C20 fragment of antibiotic TMC-151A, siphonarienal and siphonarienone

Tze Keong Lum^*, Shun Yi Wang, Teck Peng Loh

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

A highly selective and general method for the synthesis of enantiopure deoxypropionates via the iterative application of Cul-Tol-BINAP-catalyzed asymmetric conjugate addition is described. This method gives access to all possible stereoisomers since both syn- and anti-deoxypropionates were obtained in high diastereoselectivities. The usefulness of the method is further exemplified by the preparation of two marine organisms, siphonarienal and siphonarienone, from commercially available trans-2-hexenoate.

Original language	English
Pages (from-to)	761-764
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	5
DOIs	https://doi.org/10.1021/ol702715q
Publication status	Published - Mar 6 2008
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol702715q

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AU - Loh, Teck Peng

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Y1 - 2008/3/6

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A highly catalytic asymmetric conjugate addition: Synthesis of the C14-C20 fragment of antibiotic TMC-151A, siphonarienal and siphonarienone

Abstract

ASJC Scopus Subject Areas

UN SDGs

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