Stereoselective Synthesis of Coreoside D and Determination of Its Absolute Configuration
Keyword(s):
D Values
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We report the stereoselective synthesis of (3S)- and (3R)-coreoside D. The conjugated diyne in the C1–C14 moiety was synthesized through two types of palladium-catalyzed cross-coupling reaction. The introduction of the glucopyranose was achieved by a glycosylation reaction using an imidate derivative in the presence of a Lewis acid. The asymmetric center at the C3-position was constructed by the chiral-pool method using d-malic acid. The stereochemistry at the C3-position of the natural product was determined to be R by comparing the [α]D values of the synthetic stereoisomers with that reported for the natural product.
2003 ◽
Vol 681
(1-2)
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pp. 98-101
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1987 ◽
Vol 60
(9)
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pp. 3471-3473
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2001 ◽
Vol 31
(18)
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pp. 2803-2807
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