Chemical and Pharmaceutical Bulletin

Toward General Access to the Aspidosperma-Type Terpenoid Indole Alkaloids: Synthesis of the Key 3, 3-Disubstituted Piperidones through Enantioselective …

Y Yasui, H Takeda, Y Takemoto

Index: Yasui, Yoshizumi; Takeda, Hiroshi; Takemoto, Yoshiji Chemical and Pharmaceutical Bulletin, 2008 , vol. 56, # 11 p. 1567 - 1574

Full Text: HTML

Citation Number: 12

Abstract

An enantioselective intramolecular Heck-type reaction of chloroformamides has been developed for the synthesis of 3, 3-disubstituted piperidones. The desired piperidone was formed in the presence of a palladium catalyst, an optically active phosphoramidite ligand, K 3 PO 4 and Ag 3 PO 4. The obtained piperidone was converted to epieburnamonine.

~91%

Mild and selective deprotection of carbamates with Bu 4 NF

[Jacquemard, Ulrich; Beneteau, Valerie; Lefoix, Myriam; Routier, Sylvain; Merour, Jean-Yves; Coudert, Gerard Tetrahedron, 2004 , vol. 60, # 44 p. 10039 - 10047]

New submonomers for poly N-substituted glycines (peptoids)

[Uno, Tetsuo; Beausoleil, Eric; Goldsmith, Richard A.; Levine, Barry H.; Zuckermann, Ronald N. Tetrahedron Letters, 1999 , vol. 40, # 8 p. 1475 - 1478]