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Total Synthesis of (±)‐Lysergic Acid by an Intramolecular Imino‐ Diels ‐ Alder Reaction. Preliminary communication
Author(s) -
Oppolzer Wolfgang,
Francotte Eric,
Bättig Kurt
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640212
Subject(s) - chemistry , intramolecular force , lysergic acid , cycloaddition , hydroxymethyl , thermal decomposition , diels–alder reaction , medicinal chemistry , stereochemistry , diene , organic chemistry , catalysis , natural rubber
(±)‐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.