Total synthesis of (+/-)-aspidospermidine

Authors
Toczko, MA Heathcock, CH
Citation
Ma. Toczko et Ch. Heathcock, Total synthesis of (+/-)-aspidospermidine, J ORG CHEM, 65(9), 2000, pp. 2642-2645
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
9
Year of publication
2000
Pages
2642 - 2645
Database
ISI
SICI code
0022-3263(20000505)65:9<2642:TSO(>2.0.ZU;2-T
Abstract
(+/-)-Aspidospermidine (1) has been synthesized from readily available meth yl 3-ethyl-2-oxocylopentanecarboxylate (17) in 5.9% yield over 13 steps. Th e key step of the synthesis is an intramolecular cascade reaction that simu ltaneously forms the B, C, and D rings of 1. A high-yielding method of clos ing the remaining E ring is also described.