Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement |
| |
| Authors: | Smith A B Verhoest P R Minbiole K P Lim J J |
| |
| Institution: | Department of Chemistry, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu |
| |
| Abstract: | formula: see text] In this, the first of two letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and B (2), rare oxazole-containing macrolides possessing extraordinary antimitotic activity, and describe the assembly of a C(3-19) subtarget (-)-5 for the total synthesis of phorboxazole A. The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran. Dimethylaluminum chloride (Me2AlCl) proved to be the Lewis acid of choice for the Petasis-Ferrier rearrangement. |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
|
