Basavaiah, Deevi ; Krishnamacharyulu, Marimganti ; Hyma, Rachakonda Suguna ; Sarma, Pakala K. S. ; Kumaragurubaran, Nagaswamy (1999) A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids Journal of Organic Chemistry, 64 (4). pp. 1197-1200. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo981761b
Related URL: http://dx.doi.org/10.1021/jo981761b
Abstract
A simple and convenient stereoselective synthesis of [E]-α-methylcinnamic acids via the nucleophilic addition of hydride ion from sodium borohydride to methyl 3-acetoxy-3-aryl-2-methylenepropanoates followed by hydrolysis and crystallization is described. Efficacy of this methodology in the synthesis of [E]-p-(myristyloxy)-α-methylcinnamic acid, an active hypolipidemic agent, and [E]-p-(carbomethoxy)-α -methylcinnamic acid, a valuable synthon for an orally active serine protease inhibitor, is also demonstrated.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 3964 |
| Deposited On: | 13 Oct 2010 07:09 |
| Last Modified: | 17 Jan 2011 05:57 |
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