Tetrahedron

Nitroindolenines en serie vincadifformine: intermediaires d'acces a la vincamone et a un squelette azahomoaspidospermane

G Lewin, J Poisson, P Toffoli

Index: Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron, 1987 ,  vol. 43,  # 3  p. 493 - 500

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Citation Number: 8

Abstract

Vincadifformine and its 10-substituted analogs give in good yields 16-nitro indolenines of which the reactivity has been studied. By a two step process (demethoxycarbonylation and chloration on C16) nitro-indolenine 2b leads to gem-chloro-nitro 6. By an other two step sequence (NaBH3CN, NaH) nitro-indo-lenine 2c yields compound 10 via a 16→ 1 COOCH3 migration. By heating compounds 6 and 10 in CF3COOH, rearranged products are ...