Synthetic Studies Toward (+)-Spongidepsin

A convergent enantiomerically controlled synthetic effort toward (+)‐spongidepsin is reported. The synthesis benefits from the use of readily available and inexpensive starting materials like D‐mannitol and (−)‐β‐citronellene. Key transformations include Evans asymmetric methylation, Mitsunobu ester...

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Veröffentlicht in:Helvetica chimica acta 2013-08, Vol.96 (8), p.1590-1600
Hauptverfasser: Venkateswar Reddy, Guvvala, Satish Chandra Kumar, Rotte, Shankaraiah, Gundeti, Suresh Babu, Katragadda, Madhusudana Rao, Janaswamy
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Sprache:eng
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Zusammenfassung:A convergent enantiomerically controlled synthetic effort toward (+)‐spongidepsin is reported. The synthesis benefits from the use of readily available and inexpensive starting materials like D‐mannitol and (−)‐β‐citronellene. Key transformations include Evans asymmetric methylation, Mitsunobu esterification, (1H‐benzotriazol‐1‐yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP)‐mediated amide formation for the preparation of a fully functionalized acyclic precursor, and ring‐closing metathesis (RCM).
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201200519