A C-glycosidation approach to the central core of amphidinol 3: synthesis of the c39-c52 fragment.
[reaction: see text] 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.
de Vicente
Javier
J
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Betzemeier
Bodo
B
Rychnovsky
Scott D
SD
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D000095722:Amphidinols
D000475:Alkenes; D006027:Glycosides; D011714:Pyrans; C438973:amphidinol 3; D000095722:Amphidinols