Tetrahedron

Stereoselective total syntheses of (−)-desoxoprosopinine and (−)-desoxoprosophylline: palladium (O)-catalyzed intramolecular N-alkylation for the key piperidine ring …

…, Y Nigawara, E Nishino, I Takagi, K Maeda, K Tadano…

Index: Takao; Nigawara; Nishino; Takagi; Maeda; Tadano; Ogawa Tetrahedron, 1994 , vol. 50, # 19 p. 5681 - 5704

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Citation Number: 65

Abstract

Intramolecular N-alkylation of D-glucose-derived substrate 21E proceeded in an S N 2′ mode smoothly in the presence of a Pd(O)catalyst and n-Bu 4 NI. The major cyclization product, a 2,6-dialkylated piperidine 22t, was effectively converted into the title alkaloids. ... Two prosopis alkaloids (−)-desoxoprosophylline (1) and (−)-desoxoprosophylline (2) were synthesized stereoselectively. The total syntheses featured by a Pd(O)-catalyzed intramolecular N- ...