Volume 24, Issue 14
Natural Products
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ChemInform Abstract: Synthesis of 20-Deethylsilicine from a Second-Generation 2-Cyano-. delta.3-piperidine Synthon.

D. S. GRIERSON

D. S. GRIERSON

Inst. Chim. Subst. Nat., 91198 Gif-sur-Yvette, Fr.

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J.-L. BETTIOL

J.-L. BETTIOL

Inst. Chim. Subst. Nat., 91198 Gif-sur-Yvette, Fr.

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I. BUCK

I. BUCK

Inst. Chim. Subst. Nat., 91198 Gif-sur-Yvette, Fr.

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H.-P. HUSSON

H.-P. HUSSON

Inst. Chim. Subst. Nat., 91198 Gif-sur-Yvette, Fr.

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M. RUBIRALTA

M. RUBIRALTA

Inst. Chim. Subst. Nat., 91198 Gif-sur-Yvette, Fr.

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A. DIEZ

A. DIEZ

Inst. Chim. Subst. Nat., 91198 Gif-sur-Yvette, Fr.

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First published: April 6, 1993

Abstract

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ChemInform Abstract

Zn(II)-catalyzed reaction of the title synthon (II) with indole (I) gives the indolylmethyl(phenylsulfonyl)piperidinecarbonitrile (III). This is consecutively treated with AgBF4 and diethyl sodiomalonate (IV) to form the δ2-piperidine (V) which is subjected to catalytic hydrogenation and acid-mediated cyclization, yielding the target alkaloid derivative (VII).

chemical structure image

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