THE FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CHEMOTACTIC FACTOR SIRENIN BY AN INTRAMOLECULAR [2+1] CYCLIZATION USING A NEW CHIRAL CATALYST

Authors
GANT TG NOE MC COREY EJ
Citation
Tg. Gant et al., THE FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CHEMOTACTIC FACTOR SIRENIN BY AN INTRAMOLECULAR [2+1] CYCLIZATION USING A NEW CHIRAL CATALYST, Tetrahedron letters, 36(48), 1995, pp. 8745-8748
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
48
Year of publication
1995
Pages
8745 - 8748
Database
ISI
SICI code
0040-4039(1995)36:48<8745:TFESOT>2.0.ZU;2-A
Abstract
A simple, highly enantioselective synthesis of sirenin (1) (bioactive form) has been developed which depends on the intramolecular [2 + 1] c ycloaddition reaction of diazo ester 5 to form bicyclic ester 6 (95:5 enantioselectivity) using a new and remarkably stable monomeric chiral Cu(I) complex (2) whose structure was proven by X-ray diffraction ana lysis.