Sabitha, Gowravaram ; Vasudeva Reddy, D. ; Senkara Rao, A. ; Yadav, J. S. (2010) Stereoselective formal synthesis of aspergillide A Tetrahedron Letters, 51 (32). pp. 4195-4198. 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.2010.06.013
Abstract
The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI2-induced intramolecular reductive cyclization as well as by using sequential α-aminooxylation, Horner-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | 14-membered Macrolide; Z-isomer; Cross-metathesis; RCM; SmI2; α-aminooxylation; Oxa-Michael |
| ID Code: | 59601 |
| Deposited On: | 07 Sep 2011 05:58 |
| Last Modified: | 07 Sep 2011 06:14 |
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