Formal total synthesis of (+)-trehazolin. Application of an asymmetric aldol-olefin metathesis approach to the synthesis of functionalized cyclopentenes

Authors
Crimmins, MT Tabet, EA
Citation
Mt. Crimmins et Ea. Tabet, Formal total synthesis of (+)-trehazolin. Application of an asymmetric aldol-olefin metathesis approach to the synthesis of functionalized cyclopentenes, J ORG CHEM, 66(11), 2001, pp. 4012-4018
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
11
Year of publication
2001
Pages
4012 - 4018
Database
ISI
SICI code
0022-3263(20010601)66:11<4012:FTSO(A>2.0.ZU;2-H
Abstract
An asymmetric synthesis of the aminocyclopentitol pseudosugar of trehazolin has been completed. The synthesis hinges on an asymmetric aldol-ring closi ng metathesis strategy to construct the five-membered ring with control of both the relative and absolute stereochemistry.