Stereoselective synthesis of revised structure of stagonolide G

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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Veröffentlicht in:Tetrahedron letters 2014-01, Vol.55 (3), p.616-618
Hauptverfasser: Rajendra Prasad, K., Venkanna, A., Babu, K. Suresh, Prasad, A.R., Rao, J. Madhusudana
Format: Artikel
Sprache:eng
Schlagworte:
Asymmetry
BAIB/TEMPO oxidation
Hydrogenation
Jacobsen resolution
Lactonization
Nucleophiles
Oxidation
Reaction kinetics
Regioselective epoxide opening
Sharpless asymmetric dihydroxylation
Synthesis (chemistry)
Tetrahedrons
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Beschreibung
Zusammenfassung: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.11.071