Total synthesis of (-)-cylindricine C

Authors
Molander, GA Ronn, M
Citation
Ga. Molander et M. Ronn, Total synthesis of (-)-cylindricine C, J ORG CHEM, 64(14), 1999, pp. 5183-5187
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
14
Year of publication
1999
Pages
5183 - 5187
Database
ISI
SICI code
0022-3263(19990709)64:14<5183:TSO(C>2.0.ZU;2-S
Abstract
(-)-Cylindricine C has been synthesized from commercially available (S)-(-) -1,2,4-butanetriol in 11 steps with an overall yield of 12%. The key step u tilizes a CrCl2 reduction of an azide to form the corresponding amine with a subsequent double Michael addition to create the tricyclic skeleton of cy lindricine from a monocyclic substrate.