Stereoselective Total Synthesis of Tarchonanthuslactone and Formal Synthesis of (-)-Colletol

J. S. Yadav; P. Murali Krishna Reddy; Manoj K. Gupta; Ch. Janardhana Chary

doi:10.1055/s-2007-990850

PAPER

Stereoselective Total Synthesis of Tarchonanthuslactone and Formal Synthesis of (-)-Colletol

J. S. Yadav*, P. Murali Krishna Reddy, Manoj K. Gupta, Ch. Janardhana Chary
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Abstract

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Abstract

A simple and efficient stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol is described using as the key steps Jacobsen’s kinetic resolution and a Sharpless asymmetric epoxidation. The synthesis of tarchonanthuslactone and the seco acid proceeded in 14% and 13% overall yield, respectively, starting from chiral (R)-propylene oxide.

Keywords

hydrolytic kinetic resolution - PMB acetal formation - Sharpless asymmetric epoxidation - lactonization - one-pot oxidation/alkenation - esterification

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References

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