Tetrahedron p. 493 - 500 (1987)
Update date:2022-08-16
Topics:
Lewin, G.
Poisson, J.
Toffoli, P.
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-indolenine 2c yields compound 10 via a 16 -> 1 COOCH3 migration.By heating compounds 6 and 10 in CF3COOH, rearranged products are obtained : vincamone 5 from 6 and azahomoaspidospermane 13 from 18.Mechanisms of formation of 5, 10 and 13 are discussed.
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