ja6b03533_si_001.pdf (4.73 MB)
Total Synthesis and Stereochemical Assignment of Callyspongiolide
journal contribution
posted on 2016-05-26, 12:23 authored by Jingjing Zhou, Bowen Gao, Zhengshuang Xu, Tao YeTotal synthesis of
four callyspongiolide stereoisomers led to unambiguous
assignment of relative and absolute stereochemistry of the natural
product. Key features of the convergent, fully stereocontrolled route
include the use of Krische allylation, Kiyooka Aldol reaction, Kociénski–Julia
olefination, Still–Gennari olefination, Yamaguchi macrocyclization,
and Sonogashira coupling reaction. Biological evaluation of the synthesized
compounds against an array of cancer cells revealed that the stereochemistry
of the macrolactone core played an important role.
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cancer cellscompoundconvergentSonogashiraarrayolefinationrolestereochemistryCallyspongiolideKiyooka Aldol reactionsynthesiscallyspongiolide stereoisomersStereochemical AssignmentassignmentBiological evaluationYamaguchi macrocyclizationKey featuresstereocontrolled routemacrolactone coreTotal SynthesisKrische allylationKocie
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