Stereoselective total synthesis of dinemasone A by double intramolecular hetero-Michael addition (DIHMA)

The first total synthesis of dinemasone A, a bioactive metabolite with a spiroketal moiety, is described. The main strategy for the construction of the spiroketal unit involves a double intramolecular hetero-Michael addition (DIHMA) of an ynone moiety. The thus obtained axial-equatorial mono anomeri...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-10, Vol.10 (40), p.8119-8124
Main Authors: Sharma, Gangavaram V M, Srikanth, Gourishetty, Reddy, Pothula Purushotham
Format: Article
Language:English
Subjects:
Butanols - chemistry
Mannitol - analogs & derivatives
Mannitol - chemistry
Models, Molecular
Molecular Conformation
Pyrones - chemical synthesis
Pyrones - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:The first total synthesis of dinemasone A, a bioactive metabolite with a spiroketal moiety, is described. The main strategy for the construction of the spiroketal unit involves a double intramolecular hetero-Michael addition (DIHMA) of an ynone moiety. The thus obtained axial-equatorial mono anomeric spiroketal, on spiroepimerization with ZnBr(2), was converted into the requisite axial-axial double anomeric spiroketal. The ynone moiety with four stereocentres, was prepared from a chiral propargylic alcohol (C5-C11 fragment) and a dihydroxy aldehyde (C1-C4 fragment), which in turn were obtained from D-mannitol and crotyl alcohol respectively.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26396c