Total synthesis of (+)-zaragozic acid C |
| |
Authors: | Armstrong A Barsanti P A Jones L H Ahmed G |
| |
Institution: | School of Chemistry, University of Nottingham, Nottingham NG7 2RD, U. K. A.Armstrong@ic.ac.uk |
| |
Abstract: | A total synthesis of (+)-zaragozic acid C is described. Key features of the synthesis are the use of a double Sharpless asymmetric dihydroxylation reaction of diene 6 to control stereochemistry at four contiguous stereocenters from C3 to C6; the introduction of the C1-side chain by reaction between the anion derived from the dithiane monosulfoxide 27 and the core aldehyde 12; a high yielding, acid-mediated simultaneous acetonide deprotection-dithiane removal-ketalization procedure leading exclusively to the 2, 8-dioxabicyclo3.2.1]octane core 34; and a novel triple oxidation procedure allowing installation of the tricarboxylic acid. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|