Yadav, J. S. ; Mysorekar, Sudha V. ; Rama Rao, A. V. (1989) Synthesis of (IR)-(+)-cis-chrysanthemic acid Tetrahedron, 45 (23). pp. 7353-7360. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)89196-1
Abstract
A synthesis of (IR)-cis-chrysanthemic acid from (R,R)-tartaric acid is described. The diol 8 was converted to the mono MEM protected compound 8b. Dehydration of the tertiary alcohol using methanesulfonyl chloride-triethylamine-D M A P and treatment of the resulting product with lithium in liquid ammonia afforded 10. The diazoester of 10 was subjected to intramolecular cyclopropanation using a soluble copper complex to obtain 12. Cleavage of the MEM ether, dehydration of the tertiary alcohol followed by reductive cleavage with lithium in liquid ammonia gave the title compound.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 60426 |
| Deposited On: | 09 Sep 2011 03:46 |
| Last Modified: | 05 Jul 2012 11:44 |
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