ChemInform Abstract: Enantioselective Total Synthesis of Taurospongin A.

✍ Scribed by Helene Lebel; Eric N. Jacobsen

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199923286

✦ Synopsis

Enantioselective Total Synthesis of Taurospongin A. -Taurospongin A (VIII), a naturally occurring fatty acid derivative, is synthesized by using highly effective asymmetric catalytic reactions to set each of the three stereocenter independently. This fact would allow also access to all eight stereoisomers of the core structure. The starting epoxide (I) is provided with high optical purity by kinetic resolution of the racemate catalyzed by a chromium Salen complex. The ester precursor for the Tbs-protected β-hydroxybutyryl part of ynone (II) is obtained with 99% e.e. by asymmetric catalytic hydrogenation of methyl acetoacetate as reported in literature. - (LEBEL, HELENE; JACOBSEN,