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

Vijaya Lingam Manthati, Danielle Grée, René Grée

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3825-3829
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
StatePublished - Aug 26 2005

Fingerprint

difluorides
synthesis
leukotriene B3

Keywords

  • Eicosanoids
  • Enantioselectivity
  • Fluorine
  • Leukotrienes
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B3 . / Manthati, Vijaya Lingam; Grée, Danielle; Grée, René.

In: European Journal of Organic Chemistry, No. 17, 26.08.2005, p. 3825-3829.

Research output: Contribution to journalArticle

Manthati, Vijaya Lingam ; Grée, Danielle ; Grée, René. / Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B3 In: European Journal of Organic Chemistry. 2005 ; No. 17. pp. 3825-3829.
@article{d770c66973474fce9911afc7dbc141bf,
title = "Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B3",
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.",
keywords = "Eicosanoids, Enantioselectivity, Fluorine, Leukotrienes, Stereoselective synthesis",
author = "Manthati, {Vijaya Lingam} and Danielle Gr{\'e}e and Ren{\'e} Gr{\'e}e",
year = "2005",
month = "8",
day = "26",
doi = "10.1002/ejoc.200500200",
language = "English (US)",
pages = "3825--3829",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "17",

}

TY - JOUR

T1 - Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B3

AU - Manthati, Vijaya Lingam

AU - Grée, Danielle

AU - Grée, René

PY - 2005/8/26

Y1 - 2005/8/26

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

UR - http://www.scopus.com/inward/record.url?scp=25144448133&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=25144448133&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200500200

DO - 10.1002/ejoc.200500200

M3 - Article

AN - SCOPUS:25144448133

SP - 3825

EP - 3829

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 17

ER -