Singh, Ravi P. ; Singh, Vinod K. (2004) Facile one-step synthesis of β-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol The Journal of Organic Chemistry, 69 (10). pp. 3425-3430. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo049858n
Related URL: http://dx.doi.org/10.1021/jo049858n
Abstract
We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from α-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a α,β-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a δ-lactone, which was converted into the target compounds in two steps.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 55382 |
| Deposited On: | 18 Aug 2011 08:39 |
| Last Modified: | 18 Aug 2011 08:39 |
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