Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B3

Vijaya Lingam Manthati; Danielle Grée; René Grée

doi:10.1002/ejoc.200500200

Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B₃

Vijaya Lingam Manthati, Danielle Grée, René Grée

Biochemistry

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

20 Scopus citations

Abstract

The first synthesis of the 5,5-difluoro-(12R)- and -(12S)-leukotrienes B₃ is reported which uses a flexible and convergent strategy. The key steps involve a Sonogashira coupling between the bromodienone 4 and the propargylic difluoride 5; this is followed by a CBS type reduction to establish the (12R) or (12S) stereocenters. A final semihydrogenation, under controlled conditions, affords the required E,E,Z trienic system.

Original language	English (US)
Pages (from-to)	3825-3829
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.200500200
State	Published - Aug 26 2005

Keywords

Eicosanoids
Enantioselectivity
Fluorine
Leukotrienes
Stereoselective synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.200500200

Cite this

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abstract = "The first synthesis of the 5,5-difluoro-(12R)- and -(12S)-leukotrienes B3 is reported which uses a flexible and convergent strategy. The key steps involve a Sonogashira coupling between the bromodienone 4 and the propargylic difluoride 5; this is followed by a CBS type reduction to establish the (12R) or (12S) stereocenters. A final semihydrogenation, under controlled conditions, affords the required E,E,Z trienic system.",

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AU - Grée, Danielle

AU - Grée, René

PY - 2005/8/26

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N2 - The first synthesis of the 5,5-difluoro-(12R)- and -(12S)-leukotrienes B3 is reported which uses a flexible and convergent strategy. The key steps involve a Sonogashira coupling between the bromodienone 4 and the propargylic difluoride 5; this is followed by a CBS type reduction to establish the (12R) or (12S) stereocenters. A final semihydrogenation, under controlled conditions, affords the required E,E,Z trienic system.

AB - The first synthesis of the 5,5-difluoro-(12R)- and -(12S)-leukotrienes B3 is reported which uses a flexible and convergent strategy. The key steps involve a Sonogashira coupling between the bromodienone 4 and the propargylic difluoride 5; this is followed by a CBS type reduction to establish the (12R) or (12S) stereocenters. A final semihydrogenation, under controlled conditions, affords the required E,E,Z trienic system.

KW - Eicosanoids

KW - Enantioselectivity

KW - Fluorine

KW - Leukotrienes

KW - Stereoselective synthesis

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