STEREOSELECTIVE ISOMERIZATION OF 10-ARYLSULFENATE-11,12-DEHYDRORETINOIDS TO 9-CIS-RETINOIDS

Authors
DELERA AR CASTRO A TORRADO A LOPEZ S
Citation
Ar. Delera et al., STEREOSELECTIVE ISOMERIZATION OF 10-ARYLSULFENATE-11,12-DEHYDRORETINOIDS TO 9-CIS-RETINOIDS, Tetrahedron letters, 39(25), 1998, pp. 4575-4578
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
25
Year of publication
1998
Pages
4575 - 4578
Database
ISI
SICI code
0040-4039(1998)39:25<4575:SIO1>2.0.ZU;2-3
Abstract
The C-7-C-12 triene fragment of 9-cis-retinoids 8 was stereoselectivel y generated by treatment of propargylic alcohol 3 with phenylsulfenyl chloride/triethylamine at -78 degrees C, followed by stereospecific re duction of the resulting vinylsulfoxide (t-BuLi, MeLi, MeOH, -78 degre es C). Thus, 9-cis-retinoic acid 2, the natural ligand of the retinoid X receptor (RXR) was straightforwardly synthesized from 8 in two step s. (C) 1998 Elsevier Science Ltd. All rights reserved.