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Stereoselective synthesis of some acetylenic analogues of leukotrienes A and D

โœ Scribed by Robert N Young; Eric Champion; Jacques Y Gauthier; Thomas R Jones; Serge Leger; Robert Zamboni

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
237 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

converslon The stereocontrolled synthesls of methyl 5(E)-epoxyelcosa-7-ynoate (7) and Its to a 7.8-acetylene-LTD analog Is described. Chlral acetylene-LTA analogs are prepared followlng a novel and versatile "one pot" procedure from S(S)-benzoyloxy-5formylpentanoate (3). There has been conslderable ongolng Interest In explorlng the structural requirements for bloactlvlty of the Important blologlcal medlators, the leukotrlenes, particularly wlth respect to the degree and stereochemlstry of unsaturatlon In the polyenlc backbone. Researchers have prepared leukotrlene analogues lacking some* or all3 of the double bonds, uhlle others have Incorporated acetylenes In place of selected double bonds4 In the polyenlc system. Recent studles have suggested that leukotrlenes wlth three or even flve double bonds (I.e. LTC5) may exlst In nature.5 It Is notable that LTC: and olefln

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