Chakraborty, Tushar Kanti ; Purkait, Subhas (2008) Total synthesis of hyptolide Tetrahedron Letters, 49 (38). pp. 5502-5504. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.07.033
Abstract
The total synthesis of hyptolide, a naturally occurring α,β-unsaturated six-membered δ-lactone substituted with a polyoxygenated chain, is described. Sharpless kinetic resolution and opening of two different epoxy alcohols under two different conditions-Swern oxidation conditions and a radical reaction using Cp2TiCl-fixed the stereocenters at C-9, C-11, and C-12, respectively. Brown's asymmetric allylation reaction installed the remaining stereocenter at C-6. A RCM protocol was used for construction of the α,β-unsaturated six-membered δ-lactone moiety of the molecule.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Hyptolide; Radical Epoxide Opening; Ring-closing Metathesis |
| ID Code: | 20437 |
| Deposited On: | 20 Nov 2010 14:30 |
| Last Modified: | 20 Nov 2010 14:30 |
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