A C-Glycosidation Approach to the Central Core of Amphidinol 3:  Synthesis of the C39−C52 Fragment

A C-Glycosidation Approach to the Central Core of Amphidinol 3:  Synthesis of the C39−C52 Fragment

A concise route to an advance precursor (3) of the central core of amphidinol 3, a natural occurring polyketide, has been developed by applying a reductive lithiation as key step. The origin of the diastereoselectivity of this reaction was comprehensively studied for nucleophilic C-glycoside donor 5...

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Veröffentlicht in:Organic letters 2005-04, Vol.7 (9), p.1853-1856
Hauptverfasser: de Vicente, Javier, Betzemeier, Bodo, Rychnovsky, Scott D
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemical synthesis
Alkenes - chemistry
Animals
Dinoflagellida - chemistry
Glycosides - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
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Zusammenfassung:A concise route to an advance precursor (3) of the central core of amphidinol 3, a natural occurring polyketide, has been developed by applying a reductive lithiation as key step. The origin of the diastereoselectivity of this reaction was comprehensively studied for nucleophilic C-glycoside donor 5 and differently protected analogues.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050477l