Yadav, Jhillu S. ; Raghavendra Rao, K. V. ; Ravindar, K. ; Subba Reddy, B. V. (2011) Total synthesis of (+)-bourgeanic acid utilizing desymmetrization strategy European Journal of Organic Chemistry, 2011 (1). pp. 58-61. ISSN 1434-193X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...
Related URL: http://dx.doi.org/10.1002/ejoc.201001199
Abstract
A highly stereoselective total synthesis of an aliphatic depside (+)-bourgeanic acid via (-)-hemibourgeanic acid and bourgeanic lactone is described. The key steps involved in this synthesis are desymmetrization of bicyclic olefin with Brown's asymmetric hydroboration, Gillman's reaction, TEMPO-BAIB mediated selective oxidation of 1,3-diol, Yamaguchi macro-lactonization and LiOH-mediated partial hydrolysis of unusually stable eight-membered cyclic dilactone.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons. |
| Keywords: | Total Synthesis; Asymmetric Synthesis; Natural Products; Bourgeanic Acid |
| ID Code: | 63100 |
| Deposited On: | 28 Sep 2011 03:49 |
| Last Modified: | 28 Sep 2011 03:49 |
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