Volume 28, Issue 50
Heterocyclic Compounds
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ChemInform Abstract: Highly Stereoselective Construction of trans-(2,3)-cis(2,6)- Trisubstituted Piperidines: An Application to the Chiral Synthesis of Dendrobates Alkaloids.

N. TOYOOKA

N. TOYOOKA

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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K. TANAKA

K. TANAKA

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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T. MOMOSE

T. MOMOSE

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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J. W. DALY

J. W. DALY

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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H. M. GARRAFFO

H. M. GARRAFFO

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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First published: 02 August 2010

Abstract

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ChemInform Abstract

Treatment of the piperidines (I) with cuprates leads to trans-(2,3)- cis-(2,6)-trisubstituted piperidines in a highly stereoselective manner. The latter are useful chiral building blocks for the synthesis of 5,8-disubstituted indolizidines such as (V) and 1,4-disubstituted quinolizidines like (VII) found in Dendrobates alkaloids.

chemical structure image

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