Yadav, J. S. ; Rajaiah, G. ; Krishnam Raju, A. (2003) A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone Tetrahedron Letters, 44 (31). pp. 5831-5833. 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/S0040-4039(03)01413-8
Abstract
A concise and flexible stereoselective route to synthesize both enantiomers of the highly functionalized α,β-unsaturated-δ-lactones, altholactone and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulphonic acid. The synthesis of both enantiomers of altholactone and isoaltholactone has been achieved in a concise and highly enantioselective manner.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Altholactone; Isoaltholactone; Cinnamyl Alcohol; Sharpless Asymmetric Epoxidation; Sharpless Asymmetric Dihydroxylation |
ID Code: | 60393 |
Deposited On: | 09 Sep 2011 03:51 |
Last Modified: | 09 Sep 2011 03:51 |
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