Synthesis of optically active indolizidines: (-)-8a-epi-dendroprimine and (-)-7,8-dehydro-5,6-dimethylindolizidine

Citation
M. Diederich et U. Nubbemeyer, Synthesis of optically active indolizidines: (-)-8a-epi-dendroprimine and (-)-7,8-dehydro-5,6-dimethylindolizidine, SYNTHESIS-S, (2), 1999, pp. 286-289
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
1999
Pages
286 - 289
Database
ISI
SICI code
0039-7881(199902):2<286:SOOAI(>2.0.ZU;2-4
Abstract
Indolizidinones can be employed as key intermediates in efficient asymmetri c synthesis of naturally occurring indolizidine alkaloid analogues. The 5,7 -dimethylindolizidine (-)-8a-epi-dendroprimine was formed by a diastereosel ective methylation-reduction sequence of the lactam function. The (-)-5,6-d imethylindolizidine was generated via the same key step including an additi onal quasi 1,2-methyl shift: an intramolecular enamine alkylation is follow ed by regioselective reductive cyclopropane ring opening.