Enantioselective Total Synthesis of (+)-SteenkrotinA and Determination of Its Absolute Configuration

The first enantioselective total synthesis of (+)-steenkrotinA has been achieved in 18steps and 4.2% overall yield. The key features of the strategy entail a Rh-catalyzed O-H bond insertion followed by an intramolecular carbonyl-ene reaction, two sequential SmI2-mediated Ueno-Stork and ketyl-olefin...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-01, Vol.22 (3), p.959-970
Main Authors: Pan, Saiyong, Gao, Beiling, Hu, Jialei, Xuan, Jun, Xie, Hujun, Ding, Hanfeng
Format: Article
Language:English
Subjects:
Absolute configuration
Aldehydes
Aquatic birds
Carbonyls
Cascades
Chemistry
Condensation
Condensing
Construction
Enantiomers
Insertion
Inversion
Rhodium
Strategy
Synthesis
Yield
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Summary:The first enantioselective total synthesis of (+)-steenkrotinA has been achieved in 18steps and 4.2% overall yield. The key features of the strategy entail a Rh-catalyzed O-H bond insertion followed by an intramolecular carbonyl-ene reaction, two sequential SmI2-mediated Ueno-Stork and ketyl-olefin cyclizations, and a cascade intramolecular aldol condensation/vinylogous retro-aldol/aldol process with inversion of the relative configuration at the C7 position. The absolute configuration of (+)-steenkrotin A was determined based on the stepwise construction of the stereocenters during the total synthesis.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201503831