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).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
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Aryldialkylphosphatase / chemistry
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Azo Compounds / chemistry
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Carboxylic Acids / chemistry
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Catalysis
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Cyclopropanes / chemistry*
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Molecular Structure
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry
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Stereoisomerism
Substances
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Azo Compounds
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Carboxylic Acids
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Cyclopropanes
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Sesquiterpenes
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colletoic acid
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cyclopropane
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11-beta-Hydroxysteroid Dehydrogenase Type 1
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Aryldialkylphosphatase