Total Synthesis of (±)-Lysergic Acid by an Intramolecular Imino-<i>Diels-Alder</i> Reaction. Preliminary communication

Von Oppolzer, Wolfgang; Francotte, Eric; Bättig, Kurt

doi:10.1002/hlca.19810640212

Scientific article

English

Total Synthesis of (±)-Lysergic Acid by an Intramolecular Imino-Diels-Alder Reaction. Preliminary communication

ContributorsVon Oppolzer, Wolfgang; Francotte, Eric; Bättig, Kurt

Published inHelvetica chimica acta, vol. 64, no. 2, p. 478-481

Publication date1981-03-18

First online date2004-10-25

Abstract

(±)-Lysergic acid (1) has been synthesized from 4-hydroxymethyl-1-tosylindole (2) by a sequence of 9 steps. The crucial thermolysis 9 → 10 involves the in situ-generation of the transient diene III which undergoes an intramolecular cycloaddition to a C, N-double bond at 200° and at low stationary concentration of III.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, FRANCOTTE, Eric, BÄTTIG, Kurt. Total Synthesis of (±)-Lysergic Acid by an Intramolecular Imino-Diels-Alder Reaction. Preliminary communication. In: Helvetica chimica acta, 1981, vol. 64, n° 2, p. 478–481. doi: 10.1002/hlca.19810640212

Article (Published version)

Identifiers

PID : unige:169150
DOI : 10.1002/hlca.19810640212

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19810640212

Journal ISSN0018-019X

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Total Synthesis of (±)-Lysergic Acid by an Intramolecular Imino-Diels-Alder Reaction. Preliminary communication

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