Synthesis of enantiomerically pure (-)-(S)-brevicolline

Authors
Mahboobi, S Wiegrebe, W Popp, A
Citation
S. Mahboobi et al., Synthesis of enantiomerically pure (-)-(S)-brevicolline, J NAT PROD, 62(4), 1999, pp. 577-579
Citations number
26
Categorie Soggetti
Agricultural Chemistry","Pharmacology & Toxicology
Journal title
JOURNAL OF NATURAL PRODUCTS
ISSN journal
01633864 → ACNP
Volume
62
Issue
4
Year of publication
1999
Pages
577 - 579
Database
ISI
SICI code
0163-3864(199904)62:4<577:SOEP(>2.0.ZU;2-#
Abstract
(-)-(S)-Brevicolline (1) and related beta-carbolines were synthesized using an enantiomerically pure Michael-acceptor synthon (3). Subsequent Pictet-S pengler reaction afforded the tetrahydro-beta-carboline skeleton, which, in turn, was transformed to the beta-carboline by catalytic dehydrogenation.