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) |
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Pages (from-to) | 3825-3829 |
Number of pages | 5 |
Journal | European Journal of Organic Chemistry |
Issue number | 17 |
DOIs | |
State | Published - Aug 26 2005 |
Keywords
- Eicosanoids
- Enantioselectivity
- Fluorine
- Leukotrienes
- Stereoselective synthesis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry