TOTAL SYNTHESIS OF (-)-DESOXOPROSOPININE VIA THE DIASTEREOSELECTIVE REDUCTION OF HOMOCHIRAL2-ACYL-N-BOC-OXAZOLIDINES

Authors
AGAMI C COUTY F MATHIEU H
Citation
C. Agami et al., TOTAL SYNTHESIS OF (-)-DESOXOPROSOPININE VIA THE DIASTEREOSELECTIVE REDUCTION OF HOMOCHIRAL2-ACYL-N-BOC-OXAZOLIDINES, Tetrahedron letters, 39(21), 1998, pp. 3505-3508
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
21
Year of publication
1998
Pages
3505 - 3508
Database
ISI
SICI code
0040-4039(1998)39:21<3505:TSO(VT>2.0.ZU;2-7
Abstract
(-)-Desoxoprosopinine was synthesised from (R)-phenylglycinol as the c hiral source. The three distinct steps used for the construction of th e three stereogenic centers of the target were all highly diastereosel ective. These steps include a reduction of a homochiral N-Boc-2-acyl o xazolidine and the stereoselectivity of this reaction can be explained by a non chelated model. An original N-debenzylation of the phenyl gl ycinol appendage was devised in this synthesis. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.