Samajdar, Susanta ; Ghatak, Anjan ; Banerjee, Shyamapada ; Ghosh, Subrata (2001) High diastereoselectivity in claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (±)-β-necrodol Tetrahedron, 57 (10). pp. 2011-2014. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)00019-9
Abstract
Total synthesis of the monoterpene β -necrodol has been accomplished. The key step involves an ortho-ester Claisen rearrangement in a highly sterically congested cyclopentane derivative resulting in a high level of 1,3-trans diastereoselection. A novel photo-induced decarboxylation of the obtained γ ,δ -unsaturated acid afforded β -necrodol.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Terpenes and Terpenoids; Claisen Rearrangement; Decarboxylation; Photochemistry |
| ID Code: | 12364 |
| Deposited On: | 10 Nov 2010 06:21 |
| Last Modified: | 14 Feb 2011 04:10 |
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