SYNTHESIS OF 19(RS)-O-TBDMS-LTA4 METHYL-E STER

Authors
PASTOURET A VIDAL JP DURAND T GIRARD JP ROSSI JC
Citation
A. Pastouret et al., SYNTHESIS OF 19(RS)-O-TBDMS-LTA4 METHYL-E STER, Bulletin de la Societe chimique de France, 130(2), 1993, pp. 206-213
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
130
Issue
2
Year of publication
1993
Pages
206 - 213
Database
ISI
SICI code
0037-8968(1993)130:2<206:SO1MS>2.0.ZU;2-A
Abstract
The first convergent synthesis of methyl -butyldimethylsilyloxy-5(S),6 (S)-epoxy-icosa-7(E), 9(E), ll(Z), 14(Z)-tetraenoate (19(RS)-O-TBDMS-L TA4 1) is described, using a Wittig reaction between a C1-C-11 chiral epoxydienal (from (-)-2-deoxy-D-ribose as starting material) and an (o mega - 1) functionalized phosphorus ylide, which was obtained by a rea ction of alkyl bromide and lithium alkynylide. This strategy is suffic iently general and could allow to synthesize other analogues giving ne w haptens.