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Synthesis 2014; 46(11): 1532-1538
DOI: 10.1055/s-0033-1340903
DOI: 10.1055/s-0033-1340903
paper
Total Synthesis of 6-O-Benzoylzeylenol from Diacetone Glucose
Weitere Informationen
Publikationsverlauf
Received: 27. November 2013
Accepted after revision: 13. Februar 2014
Publikationsdatum:
27. März 2014 (online)
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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 synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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