Prasad, Kavirayani R. ; Anbarasan, Pazhamalai (2007) Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (-)-isolaurepan Tetrahedron: Asymmetry, 18 (12). pp. 1419-1427. ISSN 0957-4166
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetasy.2007.05.014
Abstract
The enantioselective synthesis of α-benzyloxy aldehydes containing a terminal alkene was carried out from chiral pool L-(+)-tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7-cis-disubstituted oxepane (−)-isolaurepan.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 105814 |
| Deposited On: | 21 Dec 2017 12:04 |
| Last Modified: | 21 Dec 2017 12:04 |
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