Synthesis 2014; 46(11): 1532-1538
DOI: 10.1055/s-0033-1340903
paper
© Georg Thieme Verlag Stuttgart · New York

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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Publikationsverlauf

Received: 27. November 2013

Accepted after revision: 13. Februar 2014

Publikationsdatum:
27. März 2014 (online)


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.

Supporting Information