SYNTHESIS OF NONPEPTIDE SCAFFOLDING DOMAINS VIA A TOTALLY STEREOSELECTIVE IODOLACTONIZATION PROTOCOL

Authors
HAUSKE JR JULIN SM
Citation
Jr. Hauske et Sm. Julin, SYNTHESIS OF NONPEPTIDE SCAFFOLDING DOMAINS VIA A TOTALLY STEREOSELECTIVE IODOLACTONIZATION PROTOCOL, Tetrahedron letters, 34(31), 1993, pp. 4909-4912
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
31
Year of publication
1993
Pages
4909 - 4912
Database
ISI
SICI code
0040-4039(1993)34:31<4909:SONSDV>2.0.ZU;2-S
Abstract
Exposure of the chiral, non-racemic, allylic ester 7 to LDA/TMSCl prov ides acid 8 and subsequent iodolactonization of 8 provides one lactone (9) with total stereoselectivity. X-ray analysis of the corresponding alpha-methylbenzylamides of 8 and 9 confirmed the absolute stereochem istry of the trans-anti-trans lactone (9). The synthesis is completed by treatment of 9 with the enolate of t-butyl acetate affording tetrah ydrofuranyl derivative 12.