Authors
Timothy F Jamison, Soroosh Shambayati, William E Crowe, Stuart L Schreiber
Publication date
1997/5/14
Journal
Journal of the American Chemical Society
Volume
119
Issue
19
Pages
4353-4363
Publisher
American Chemical Society
Description
The diterpene (+)-epoxydictymene has been synthesized in 20 steps using the asymmetry of (R)-pulegone and several substrate-controlled diastereoselective reactions to prepare the natural product in its natural configuration. Three of the four rings were assembled with two consecutive intramolecular reactions involving dicobalt hexacarbonyl complexes of alkynes: a Lewis acid-promoted Nicholas reaction and a Pauson−Khand reaction. The construction of the strained trans-3-oxabicyclo[3.3.0]octane ring system of the natural product presented a significant challenge. To this end, several radical and anionic cyclizations were studied, the latter leading to (+)-epoxydictymene.
Total citations
Scholar articles
TF Jamison, S Shambayati, WE Crowe, SL Schreiber - Journal of the American Chemical Society, 1997