Stereoselective Synthesis of the 5,5‐Difluoro‐(12 R )‐ and ‐(12 S )‐Leukotrienes B 3 | Zendy

Lingam Manthati Vijaya | Zendy; Grée Danielle | Zendy; Grée René | Zendy

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Stereoselective Synthesis of the 5,5‐Difluoro‐(12 R )‐ and ‐(12 S )‐Leukotrienes B 3

Author(s) -

Lingam Manthati Vijaya,

Grée Danielle,

Grée René

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500200

Subject(s) - chemistry , sonogashira coupling , stereocenter , stereoselectivity , convergent synthesis , stereochemistry , total synthesis , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , palladium

The first synthesis of the 5,5‐difluoro‐(12 R )‐ and ‐(12 S )‐leukotrienes B 3 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 (12 R ) or (12 S ) stereocenters. A final semihydrogenation, under controlled conditions, affords the required E,E,Z trienic system. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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