Asymmetric Total Synthesis of Vindoline

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Asymmetric Total Synthesis of Vindoline
Dale L. Boger
Department of Chemistry and The Skaggs Institute
for Chemical Biology, The Scripps Research
Institute.
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J. AM. CHEM. SOC. 2010, 132, 36853687
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Key step
4 C-C bonds 3 rings 6 new stereocenters
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The substrate bearing the (Z)-enol ether also
participates in the cycloaddition cascade but not
as effectively as the (E)-enol ether.
Teoc
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Reactions of 1,3-Diphenyl-2-propanone with
Butylorganometallic Reagents in the Presence of
Cerium Chloride
J. Am.Chem. Soc. 1989, 111, 4392.
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CDI
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drgt301
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Mitsunobu activation in the absence of added
nucleophile
J. Am.Chem. Soc. 2006, 128, 10596.
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Related Alkaloids