Chandrasekhar, M. ; Chandra, Kusum L. ; Singh, Vinod K. (2003) Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide The Journal of Organic Chemistry, 68 (10). pp. 4039-4045. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0269058
Related URL: http://dx.doi.org/10.1021/jo0269058
Abstract
Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular SN2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 55359 |
| Deposited On: | 18 Aug 2011 08:39 |
| Last Modified: | 18 Aug 2011 08:39 |
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