Total Synthesis of (-)-Conophylline and

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Total Synthesis of (-)-Conophylline and
(-)-Conophyllidine
Tohru Fukuyama _at_ University of Tokyo
Angew. Chem. Int. Ed. 2011, 50, 4884 4887
Song jin 2011-06-25 Gong Group Meeting
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(-)-Conophylline , isolated from Tabernaemontana
divaricata(???) in 1992. has been found to
induce beta-cell differentiation in rat
pancreatic acinar carcinoma cells and in
cultured fetal rat pancreatic tissue
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sterically lesshindered
tin-mediated indole synthesis bubbling of argon
gas for 10 min, then reflux
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tin-mediated indole synthesis
Fukuyama, J. Am. Chem. Soc. 1994,116, 3127
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Stille coupling
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Mistunobu reaction
Appel Reaction
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PolonovskiPotier reaction
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PolonovskiPotier reaction
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Stabilizing the carbocation


Husson, J. Org. Chem. 1982, 47, 803-811
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Thank You
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Mitsunobu reaction
betaine intermediate
Nucleophile COOH, HN3, Phenol, sulfonamide
pKa ( betaine intermediate) 13
the nucleophile must have
a pKa less than 15
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Appel reaction