Short synthesis of (±)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine

doi:10.1016/S0040-4039(97)00056-7

Tetrahedron Letters

Volume 38, Issue 8, 24 February 1997, Pages 1455-1458

https://doi.org/10.1016/S0040-4039(97)00056-7 Get rights and content

Abstract

Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of 3-ethylindolo[2,3-a]quinolizidine4a (regenerated from the corresponding α-aminonitrile 4b) afforded enamine 5. Catalytic hydrogenation of compound 5 led stereoselectively to compound 6 (pseudo), which is the highly desired intermediate for the preparation of several Corynanthé alkaloids, including (±)-hirsutine 7.

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Short synthesis of (±)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine

Abstract

Tetrahedron Lett.

Tetrahedron

Heterocycles

Tetrahedron

J. Am. Chem. Soc.

Bull. Soc. Chim. Belg.