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

Oppolzer Wolfgang | Zendy; Francotte Eric | Zendy; Bättig Kurt | Zendy

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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.

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