Tetrahedron letters

An asymmetric synthesis of indole alkaloids

MF Loewe, AI Meyers

Index: Loewe, Mallory F.; Meyers, A. I. Tetrahedron Letters, 1985 , vol. 26, # 28 p. 3291 - 3294

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Citation Number: 27

Abstract

Isocyanide 2 prepared from the N-formylvalinol t-butyl ether (ref. 1a) by treatment of a DMF solution with SOCl 2 -DMF at −45°. After warming to −25°, Na 2 CO 3 , solution was added and stirred overnight. Extraction with ether and water wash gave 2 in 75% yield, bp 72° (3 torr), α D +1.76° (c 1.2, CHCl 3 ). ... The N-Li derivative of 3 (R=Li) did not give the dilithio salt on metalation, whereas the NK salt gave only a 70:30 ratio of enantiomers of 7. The N-Me ...

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