Total synthesis of (+/-)-kelsoene

Authors
Piers, E Orellana, A
Citation
E. Piers et A. Orellana, Total synthesis of (+/-)-kelsoene, SYNTHESIS-S, (14), 2001, pp. 2138-2142
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
14
Year of publication
2001
Pages
2138 - 2142
Database
ISI
SICI code
0039-7881(200111):14<2138:TSO(>2.0.ZU;2-L
Abstract
(+/-)-Kelsoene (1) has been synthesized in 15 steps from commercially avail able cyclopent-2-en-1-one. Key steps include (a) a methylenecyclopentane an nulation of cyclopent-2-en-1-one using the bifunctional cuprate reagent lit hium cyano(4-chlorobut-1-en-2-yl)cuprate and (b) a highly stereoselective [ 2+2]-photocycloaddition of ethylene to the bicyclic enone 10.