REDUCTIVE METHYLATIONS OF 2,7-DIHYDRO DERIVATIVES OF SOME OXYGENATED INDOLE ALKALOIDS LIKE RESERPINE

Authors
ROYER D DEMAINDREVILLE MD LARONZE JY LEVY J WEN R
Citation
D. Royer et al., REDUCTIVE METHYLATIONS OF 2,7-DIHYDRO DERIVATIVES OF SOME OXYGENATED INDOLE ALKALOIDS LIKE RESERPINE, Tetrahedron, 52(27), 1996, pp. 9069-9078
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
27
Year of publication
1996
Pages
9069 - 9078
Database
ISI
SICI code
0040-4020(1996)52:27<9069:RMO2DO>2.0.ZU;2-H
Abstract
The indole alkaloids tetraphylline (1a), 3-epireserpine (2a) and reser pine (3a) were transformed into the corresponding 2,7-dihydro compound s (c) by NaBH3CN in acidic medium. These latter compounds could be fur ther mono-methylated at the 1-position (compounds e) or dimethylated a t the 1- and 10- positions (compounds g) by H2CO/NaBH3CN depending on the conditions. The configurations were established on the basis of a derailed NMR study. Copyright (C) 1996 Elsevier Science Ltd