A stereospecific synthesis of (+/-)-5,8-disubstituted indolizidines and (+/-)-1,4-disubstituted quinolizidines found in poison frog skills

Authors
Michel, P Rassat, A Daly, JW Spande, TF
Citation
P. Michel et al., A stereospecific synthesis of (+/-)-5,8-disubstituted indolizidines and (+/-)-1,4-disubstituted quinolizidines found in poison frog skills, J ORG CHEM, 65(26), 2000, pp. 8908-8918
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
26
Year of publication
2000
Pages
8908 - 8918
Database
ISI
SICI code
0022-3263(200012)65:26<8908:ASSO(I>2.0.ZU;2-G
Abstract
An efficient, high-yield stereospecific route to three (+/-)-5,8-disubstitu ted indolizidines, (209B (I), 209I (II), 223J (III)) and two (+/-)-1,4-disu bstituted quinolizidines (207I (IV), 233A (V)), racemates of alkaloids foun d in the skins of neotropical and Madagascan poison frogs is reported. The structures of the natural alkaloids were thereby established by chiral GC c omparison with the exception of indolizidine 209B (I) for which a natural 2 09B could no longer be detected.