The asymmetric synthesis of the [D-8]-labeled (-)-(S)-dihydroxyverbacine, the terminal precursor in the biogenesis of the macrobicyclic spermine alkaloids aphelandrine and orantine

Authors
Nezbedova, L Drandarov, K Werner, C Hesse, M
Citation
L. Nezbedova et al., The asymmetric synthesis of the [D-8]-labeled (-)-(S)-dihydroxyverbacine, the terminal precursor in the biogenesis of the macrobicyclic spermine alkaloids aphelandrine and orantine, HELV CHIM A, 83(11), 2000, pp. 2953-2960
Citations number
20
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
83
Issue
11
Year of publication
2000
Pages
2953 - 2960
Database
ISI
SICI code
0018-019X(2000)83:11<2953:TASOT[>2.0.ZU;2-J
Abstract
The asymmetric synthesis of the unlabeled and [D-8]-labeled terminal precur sors, 4 ((-)-(S)-dihydroxyverbacine) and 19, respectively, in the biogenesi s of the spermine alkaloids aphelandrine (5) and orantine (6), respectively , is described. A partial synthesis of the alkaloid (-)-(S)-[(E)-4-methoxyc innamoyl]buchnerine (10) is also presented.