Flexible and Simple Route for the Stereoselective Synthesis of Trisubstituted γ-Butyrolactones: Total Synthesis of (+)-Blastomycinone and its Analogs

Palakodety Radha Krishna; V. V. Ramana Reddy; G. V. M. Sharma

doi:10.1055/s-2004-829173

PAPER

Flexible and Simple Route for the Stereoselective Synthesis of Trisubstituted γ-Butyrolactones: Total Synthesis of (+)-Blastomycinone and its Analogs [1]

Palakodety Radha Krishna*, V. V. Ramana Reddy, G. V. M. Sharma
D-206/B, Discovery Laboratory, Organic Chemistry Division-III, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160387; e-Mail: prkgenius@iict.res.in;

Abstract

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Abstract

A flexible route for the stereoselective synthesis of trisubstituted γ-butyrolactones, namely (+)-blastomycinone and its analogs, is devised by the Sharpless asymmetric epoxidation and the regioselective ring opening reaction with dibutylcopper lithium as the key steps to introduce the requisite alkyl chain.

Key words

(+)-blastomycinone - (-)-3-epi-blastomycinone - Sharpless asymmetric epoxidation - dibutylcopper lithium - Wittig olefination

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References

IICT Communication No. 040203.

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