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Article

Total Synthesis of the Boron-Containing Ion Carrier Antibiotic Macrodiolide Tartrolon B

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Johann Mulzer* and Markus Berger

Institut fr Organische Chemie, Universitt Wien, Whringer Strasse 38, A-1090 Wien, Austria

J. Org. Chem., 2004, 69 (3), pp 891–898

DOI: 10.1021/jo035391p

Publication Date (Web): January 13, 2004

Corresponding author. Phone: +431-4277-52190. Fax: +431-4277-52189.

, johann.mulzer@univie.ac.at

Abstract

The first total synthesis of the boron-containing macrodiolide antibiotic tartrolon B is reported in full detail. Two convergent approaches to the target compound are described, the first of which eventually failed, due to sensitive functionality. In the second, successful route the key step was a stereoselective boron-mediated aldol addition of a bicyclic acetonide protected ketone to a diene-aldehyde. In this case the synthesis could be completed without major problems, using a Yamaguchi dimerization macrolactonization endgame.

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Published In Issue February 06, 2004
Received September 24, 2003

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Article

Total Synthesis of the Boron-Containing Ion Carrier Antibiotic Macrodiolide Tartrolon B

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Syntheses of Kapakahines B and F

Total Synthesis of (−)-Acutumine

Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion

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