Synthetic studies on virantmycin. 1. Total synthesis of (±)-virantmycin and determination of its relative stereochemistry

Y Morimoto, F Matsuda, H Shirahama

Index: Morimoto, Yoshiki; Matsuda, Fuyuhiko; Shirahama, Haruhisa Tetrahedron, 1996 , vol. 52, # 32 p. 10609 - 10630

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Citation Number: 29

Abstract

The efficient and stereospecific route to the tetrahydroquinoline ring models 3 and 4 of virantmycin has been developed by means of an intramolecular nitrene addition reaction as a key step. In the NOE experiments of 4 and 3 we revealed that a ring inversion occurs in their piperidine ring system and determined the relative stereochemistry by capturing each half-chair conformer as cyclic carbamates 26 and 27, respectively. Utilizing this protocol ...