Total synthesis of 1233A
| Autor: | J. Kiegiel, Peter Michael Wovkulich, Milan R. Uskokovic, K. Shankaran |
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| Rok vydání: | 1993 |
| Předmět: | |
| Zdroj: | The Journal of Organic Chemistry. 58:832-839 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A |
| Databáze: | OpenAIRE |
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