Agrawal, Divya ; Sriramurthy, Vardhineedi ; Yadav, Veejendra K. (2006) 4, 5-Didehydro-7-silyloxymethyl-2-oxepanone and formal total syntheses of Hagen's gland lactones and trans-kumausynes Tetrahedron Letters, 47 (43). pp. 7615-7618. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2006.08.059
Abstract
A concise and enantiospecific route to the 2,6-dioxabicyclo[3.3.0]octan-3-one ring system from commercially available (R)-(+)- and (S)-(-)-glycidols is described. The key features involve ring closing metathesis to construct the 7-substituted-4,5-dehydro-2-oxepanone and its base-catalyzed single-step rearrangement into the 2,6-dioxabicyclo[3.3.0]octan-3-one skeleton. Using this strategy, formal total syntheses of (7R)-cis-Hagen's gland lactones and (+)- and (-)-trans-kumausynes have been achieved.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Ring Closing Metathesis; Rearrangement; Natural Products; Bicyclic Framework; Epoxidation |
| ID Code: | 58248 |
| Deposited On: | 31 Aug 2011 06:57 |
| Last Modified: | 31 Aug 2011 06:57 |
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