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Total Synthesis of (-)-Conophylline and (-)-Conophyllidine. Tohru Fukuyama* @ University of Tokyo. Angew. Chem. Int. Ed. 2011, 50, 4884 –4887. Song jin 2011-06-25 Gong Group Meeting. * (-)-Conophylline , isolated from Tabernaemontana divaricata( 狗牙花 ) in 1992.
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Total Synthesis of (-)-Conophylline and (-)-Conophyllidine Tohru Fukuyama* @ University of Tokyo Angew. Chem. Int. Ed. 2011, 50, 4884 –4887 Song jin 2011-06-25 Gong Group Meeting
*(-)-Conophylline , isolated from Tabernaemontana divaricata(狗牙花) in 1992. *has been found to induce beta-cell differentiation in rat pancreatic acinar carcinoma cells and in cultured fetal rat pancreatic tissue
*sterically lesshindered *tin-mediated indole synthesis *bubbling of argon gas for 10 min, then reflux
*tin-mediated indole synthesis Fukuyama, J. Am. Chem. Soc. 1994,116, 3127
Mistunobu reaction Appel Reaction
* Stabilizing the carbocation * * Husson, J. Org. Chem. 1982, 47, 803-811
Mitsunobu reaction betaine intermediate Nucleophile: COOH, HN3, Phenol, sulfonamide pKa ( betaine intermediate) ~13 the nucleophile must have a pKa less than 15