Total synthesis of (+/-)-asteriscanolide

Authors
Krafft, ME Cheung, YY Abboud, KA
Citation
Me. Krafft et al., Total synthesis of (+/-)-asteriscanolide, J ORG CHEM, 66(22), 2001, pp. 7443-7448
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
22
Year of publication
2001
Pages
7443 - 7448
Database
ISI
SICI code
0022-3263(20011102)66:22<7443:TSO(>2.0.ZU;2-O
Abstract
The total synthesis of asteriscanolide (1) has been achieved by taking adva ntage on an intermolecular Pauson-Khand cycloaddition and a ring-closing me tathesis as key bond-forming transformations. The approach incorporates the cyclooctane stereogenic center prior to ring formation. Interestingly, the ring-closing metathesis generates a new eight-membered ring with an "in-ou t" intrabridgehead relationship.