Stereoselective synthesis of 13Z retinoic acids via beta-methylenealdehydes as synthons

Authors
Valla, A Andriamialisoa, Z Giraud, M Prat, V Laurent, A Potier, P
Citation
A. Valla et al., Stereoselective synthesis of 13Z retinoic acids via beta-methylenealdehydes as synthons, TETRAHEDR L, 40(52), 1999, pp. 9235-9237
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
52
Year of publication
1999
Pages
9235 - 9237
Database
ISI
SICI code
0040-4039(199912)40:52<9235:SSO1RA>2.0.ZU;2-T
Abstract
A stereoselective synthesis of 13Z retinoic acids via beta-methylenealdehyd es is described. In methylene-de-oxo-bisubstitution reactions (Knoevenagel, Stobbe, etc.), these new synthons produce stereoselectively E olefins. Hen ce, a synthesis of 132 retinoic acids is described, via a stereospecific mo nodecarboxylation of carboxy-14-retinoic acids. (C) 1999 Published by Elsev ier Science Ltd. All rights reserved.