Synthetic studies on the phorboxazoles: a short synthesis of an epi-C23 tetrahydropyran core |
| |
Authors: | Paul A. Clarke,Jason M. Hargreaves,Rosa Marí a Rodrí guez Sarmiento |
| |
Affiliation: | a Department of Chemistry, University of York, Heslington, York, North Yorks YO10 5DD, UK b Pharmaceuticals Division, F. Hoffmann-La Roche, PRCB Bldg. 092, CH-4070 Basel, Switzerland |
| |
Abstract: | Studies on the synthesis of the anticancer natural products, the phorboxazoles have led to the synthesis of the C21-C32 penta-substituted tetrahydropyran core which is epimeric to the natural product at C23. The synthesis was achieved in only seven linear steps. The key steps were the use of a Masamune-Abiko anti-aldol reaction, the formation of a dihydropyran precursor molecule by the use of a new ‘Maitland-Japp-like’ cyclisation, and a highly diastereoselective reductive alkylation of the dihydropyran double bond, to generate the corresponding tetrahydropyran ring in an excellent yield. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|