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

Von Oppolzer, Wolfgang; Robbiani, Christian

doi:10.1002/hlca.19830660415

Scientific article

English

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

ContributorsVon Oppolzer, Wolfgang; Robbiani, Christian

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.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

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

Article (Published version)

Identifiers

PID : unige:168190
DOI : 10.1002/hlca.19830660415

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19830660415

Journal ISSN0018-019X

58views

0downloads

Creation14/04/2023 08:49:39

First validation14/04/2023 10:15:44

Update14/04/2023 10:15:44

Status update14/04/2023 10:15:44

Last indexation01/11/2024 04:48:09

Archive ouverte UNIGE

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

Technical informations