Dibromomethane as One-Carbon Source in Organic Synthesis: Formal Total Synthesis of (±)-Nephrosteranic Acid

Author: Hon Yung-Son   Hsieh Cheng-Han   Chen Hsien-Fan  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.37, Iss.10, 2007-01, pp. : 1635-1651

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Abstract

A diastereoselective formal total synthesis of (±)-nephrosteranic acid (10) is described. The key step is to introduce the α-methylene group by the ozonolysis of monosubstituted alkenes followed by reaction with a preheated mixture of CH2Br2-Et2NH. The α-methyl group of compound 10 was formed from the reduction of the corresponding α-methylene precursor.