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Scientific article
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Highly Stereoselective Total Syntheses of (±)-Chelidonine and of (±)-Norchelidonine by an Intramolecular o-Quinodimethane/Nitrostyrene-Cycloaddition

Published inHelvetica chimica acta, vol. 66, no. 4, p. 1119-1128
Publication date1983-06-15
First online date2004-10-25
Abstract

Conversion of 2-bromomethylstyrene 22 and benzocyclobutenyl carbamate 28 to the benzophenanthridine alkaloids (±)-chelidonine (1, five steps, 25% from 28) and to (±)-norchelidonine (2, six steps, 24% from 28) are described. The key step 29 → 31 involves a highly regio- and stereocontrolled intramolecular Diels-Alder reaction of the (E)-quinodimethane 30.

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Citation (ISO format)
VON OPPOLZER, Wolfgang, ROBBIANI, Christian. Highly Stereoselective Total Syntheses of (±)-Chelidonine and of (±)-Norchelidonine by an Intramolecular <i>o</i>-Quinodimethane/Nitrostyrene-Cycloaddition. In: Helvetica chimica acta, 1983, vol. 66, n° 4, p. 1119–1128. doi: 10.1002/hlca.19830660415
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ISSN of the journal0018-019X
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