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  • Title: Enantioselective total synthesis of (+)-colletoic acid via catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide.
    Author: Sawada T, Nakada M.
    Journal: Org Lett; 2013 Mar 01; 15(5):1004-7. PubMed ID: 23398353.
    Abstract:
    The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).
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