The Polonovski-Potier reaction of berbine N-oxides. Synthesis of 8-hydroxymethyl and 8-methylberbines

Authors
Suau, R Najera, F Rico, R
Citation
R. Suau et al., The Polonovski-Potier reaction of berbine N-oxides. Synthesis of 8-hydroxymethyl and 8-methylberbines, TETRAHEDRON, 56(49), 2000, pp. 9713-9723
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
49
Year of publication
2000
Pages
9713 - 9723
Database
ISI
SICI code
0040-4020(200012)56:49<9713:TPROBN>2.0.ZU;2-R
Abstract
The Polonovski-Potier reaction of trans and cis berbines N-oxides was studi ed. The 8-cyano derivative obtained from trans N-oxides were used to synthe size 8-hydroxymethyl and 8-methyl berbines. This procedure was applied to t he stereocontroled synthesis of (8R, 14S)-(-)-8-methylcanadine from (14S)-( -)-canadine. (C) 2000 Elsevier Science Ltd. All rights reserved.