An Enantioselective Total Synthesis of (+)-Peloruside A

An Enantioselective Total Synthesis of (+)-Peloruside A

Short and sweet: Chiral epoxides, prepared using (salen)cobalt‐catalyzed ring‐opening reactions, and a chromium catalyst controlled hetero‐Diels–Alder reaction were used to set most of the stereocenters in the total synthesis of the microtubule‐stabilizing agent peloruside A. The overall highly conv...

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Veröffentlicht in:Angewandte Chemie International Edition 2010-08, Vol.49 (35), p.6147-6150
Hauptverfasser: McGowan, Meredeth A., Stevenson, Christian P., Schiffler, Matthew A., Jacobsen, Eric N.
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Chromium - chemistry
Cobalt - chemistry
Cycloaddition Reaction
epoxidation
Ethylenediamines - chemistry
kinetic resolution
Kinetics
Lactones - chemical synthesis
Lactones - chemistry
natural products
Stereoisomerism
total synthesis
Tubulin Modulators - chemical synthesis
Tubulin Modulators - chemistry
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Zusammenfassung:Short and sweet: Chiral epoxides, prepared using (salen)cobalt‐catalyzed ring‐opening reactions, and a chromium catalyst controlled hetero‐Diels–Alder reaction were used to set most of the stereocenters in the total synthesis of the microtubule‐stabilizing agent peloruside A. The overall highly convergent route required only 20 steps in the longest linear sequence. MOM=methoxymethyl, TBS=tert‐butyldimethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201002177