Tandem Dihydroxylation, Hemiketalization and Conjugate Addition Leading to a Singly Anomeric Spiroketal

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 ef...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 44; no. 12; pp. 1854 - 1862
Main Authors Davy, Jason A., Moreau, Benoit, Wulff, Jeremy E.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tandem reaction
CROSS-METATHESIS
ENANTIOSELECTIVE SYNTHESIS
ASCIDIAN DIDEMNUM SP
COPE REARRANGEMENT
ABSOLUTE-CONFIGURATIONS
spiro compounds
enones
ACULEATIN-B
stereoselective synthesis
ASYMMETRIC DIHYDROXYLATION
dihydroxylation
HIV-1 PROTEASE
PROTEASE INHIBITIVE DIDEMNAKETALS
STEREOCONTROLLED SYNTHESIS
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Summary: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.
ISSN:0039-7881
DOI:10.1055/s-0031-1290817