Stereodivergent synthesis of (-)- and (+)-slaframine from gamma-hydroxy-alpha,beta-unsaturated sulfones

Authors
Carretero, JC Arrayas, RG
Citation
Jc. Carretero et Rg. Arrayas, Stereodivergent synthesis of (-)- and (+)-slaframine from gamma-hydroxy-alpha,beta-unsaturated sulfones, SYNLETT, (1), 1999, pp. 49-52
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
1
Year of publication
1999
Pages
49 - 52
Database
ISI
SICI code
0936-5214(199901):1<49:SSO(A(>2.0.ZU;2-O
Abstract
A stereodivergent synthesis of either (-)- or (+)-slaframine from the readi ly available gamma-hydroxy-alpha, beta-unsaturated sulfone 3 is described. Key steps are the complete kinetic separation of the diastereomer mixture c is 6a+6b by reaction with Me3Al and the efficient construction of the indol izidine skeleton by intramolecular alkylation of the alpha-sulfonyl carbani on of 8a and 8b.