Stereoselective synthesis of revised structure of stagonolide G

A concise total synthesis of the revised structure of stagonolide G has been achieved in 11 steps and with an overall yield of 31.7%. Key reaction sequence includes BAIB/TEMPO mediated tandem oxidation and lactonization, Lindlar’s hydrogenation, regioselective epoxide opening by an in situ generated...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 3; pp. 616 - 618
Main Authors Rajendra Prasad, K., Venkanna, A., Babu, K. Suresh, Prasad, A.R., Rao, J. Madhusudana
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.01.2014
Elsevier
Subjects
Asymmetry
BAIB/TEMPO oxidation
Chemistry
Chemistry, Organic
Hydrogenation
Jacobsen resolution
Lactonization
Nucleophiles
Oxidation
Physical Sciences
Reaction kinetics
Regioselective epoxide opening
Science & Technology
Sharpless asymmetric dihydroxylation
Synthesis (chemistry)
Tetrahedrons
BAIB/TEMPO oxidation
Lactonization
Jacobsen resolution
Regioselective epoxide opening
Sharpless asymmetric dihydroxylation
ASYMMETRIC DIHYDROXYLATION
STAGONOSPORA-CIRSII
POTENTIAL MYCOHERBICIDE
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Summary:A concise total synthesis of the revised structure of stagonolide G has been achieved in 11 steps and with an overall yield of 31.7%. Key reaction sequence includes BAIB/TEMPO mediated tandem oxidation and lactonization, Lindlar’s hydrogenation, regioselective epoxide opening by an in situ generated alkynyl as nucleophile, Sharpless asymmetric dihydroxylation, and Jacobsen kinetic resolution.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.11.071