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Synthesis 2012; 44(12): 1854-1862
DOI: 10.1055/s-0031-1290817
DOI: 10.1055/s-0031-1290817
special topic
Tandem Dihydroxylation, Hemiketalization and Conjugate Addition Leading to a Singly Anomeric Spiroketal
Further Information
Publication History
Received: 29 February 2012
Accepted: 13 March 2012
Publication Date:
25 April 2012 (online)
Abstract
A novel, highly stereoselective tandem dihydroxylation, hemiketalization and conjugate addition reaction is reported that transforms a linear meso-functionalized bis-enone into a substituted singly anomeric spiroketal, effectively controlling six stereocenters in a single operation. As part of an effort to explore the thermodynamic consequences of establishing the singly anomeric spiroketal in this system, the assembly of a related fully anomeric spiroketal possessing an unusual ketal-spiroketal-ketal framework is demonstrated.
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