Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an L-glutamic acid derivative

Authors
Andres, JM de Elena, N Pedrosa, R Perez-Encabo, A
Citation
Jm. Andres et al., Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an L-glutamic acid derivative, TETRAHEDR-A, 12(10), 2001, pp. 1503-1509
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
10
Year of publication
2001
Pages
1503 - 1509
Database
ISI
SICI code
0957-4166(20010622)12:10<1503:SSO(A(>2.0.ZU;2-7
Abstract
A stereodivergent synthesis of threo and erythro aza-muricatacin. a non-nat ural aza-analogue of the bioactive annonaceous acetogenin muricatacin, is p resented. The configuration of the C(5) stereocenter is controlled by diast ereoselective alkylation of alpha -dibenzylamino aldehyde I or diastercosel ective reduction of alpha -dibenzylamino ketone 3. (C) 2001 Elsevier Scienc e Ltd. All rights reserved.