Total Synthesis of 6-O-Benzoylzeylenol from Diacetone Glucose

Post Sai Reddy; Gangavaram V. M. Sharma

doi:10.1055/s-0033-1340903

Synthesis, Table of Contents

Synthesis 2014; 46(11): 1532-1538
DOI: 10.1055/s-0033-1340903

paper

Total Synthesis of 6-O-Benzoylzeylenol from Diacetone Glucose

Post Sai Reddy*

Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Email: saireddypost@gmail.com Fax: +91(40)27160757

,

Gangavaram V. M. Sharma

Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Email: saireddypost@gmail.com Fax: +91(40)27160757

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Abstract

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Abstract

A total synthesis of 6-O-benzoylzeylenol from diacetone glucose is described. The key steps were a crossed aldol–Cannizzaro reaction to create a quaternary carbon stereocenter, and cyclization through ring closure metathesis (RCM). Of the four stereogenic centers, two were derived from diacetone glucose, the quaternary stereocenter was created by means of the crossed aldol–Cannizzaro reaction, and the fourth stereogenic center was produced by a Sharpless asymmetric epoxidation. Finally, cyclization through RCM and deprotection by removal of a benzyl group with titanium(IV) chloride gave the target molecule.

Key words

ring closure - metathesis - aldol reactions - Cannizzaro reactions - stereoselective synthesis

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References

References

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