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Conformationally restricted leukotriene antagonists. Synthesis of some leukotriene D4 analogs from D-xylose

โœ Scribed by Jeffrey S. Sabol; Robert J. Cregge

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
142 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Lewis acid catalyzed allylation of diacetyl-D-xylal 2 is stereoselectlve for ~-C-glycoside 2b, a result used in the syntheses of pyrans 8a, b, from D-xylose. Vhile pursuing approaches to the stereocontrolled syntheses of conformationally-restrlcted LTD 4 receptor antagonists, we became aware of a highly stereoselectlve route to C1-allylated OAc & OAc c,~ _ ,~,,,,OAc ~OAc , ,o

2 (R=H) ~ 2~

glycosides bearing C2-C s unsaturation t in which reaction of D-glucal triacetate 1 with allyltrimethylsilane (ATMS) under Lewis acid activation led to la and Ib in a ratio of 16:1. We felt that this approach could be used as an entry into the synthesis of novel, conformation-

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The stereocontrolled synthesis of conformationally restricted LTD4 analogs 2a. b is described. Epoxidation of enone 4 affords a 2.4:1 mixture of trans-epoxide 5 and cis-epoxide 9. Stereocontrolled elaboration of each epoxide to final product involves stereoselective Wittig olefination to Z-olefins 6

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A total convergent synthesis of leukotriene (+)-LTB4 has been carried out via two enantiomerically pure CY-hydroxyaldehydes,chiral key intermediates both obtained from D-mannitol and connected at a four carbon atoms interval by Wittig reactions. f)J. Rokach, J. Adams. Act. Res.,