A TOTAL ASYMMETRIC-SYNTHESIS OF (-)-SUAVEOLINE

Authors
BAILEY PD MORGAN KM
Citation
Pd. Bailey et Km. Morgan, A TOTAL ASYMMETRIC-SYNTHESIS OF (-)-SUAVEOLINE, Chemical communications, (12), 1996, pp. 1479-1480
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
12
Year of publication
1996
Pages
1479 - 1480
Database
ISI
SICI code
1359-7345(1996):12<1479:ATAO(>2.0.ZU;2-D
Abstract
A new total synthesis of (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%); key steps include a high yielding cis-specifi c Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons/alkylati on procedure, a vinylogous Thorpe cyclization and the direct formation of a pyridine from a 1,5-dinitrile.