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Synthesis of a tritium labelled pyrrolizidine alkaloidisenecioyl retronecine
Author(s) -
Hsu I. C.,
Allen J. R.
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110110
Subject(s) - pyrrolizidine , chemistry , pyrrolizidine alkaloid , acylation , alkaloid , hydrolysis , chloride , stereochemistry , organic chemistry , catalysis
Retronecine (7β‐hydroxy‐1‐hydoxymethyl‐1,2‐dehydro‐8α‐pyrrolizidine) (II) which is prepared from the hydrolysis of monocrotaline (I) was oxidized with manganese dioxide in the presence of potassium cyanide to methyl 1,2‐dehydro‐7β‐hydroxy‐8α‐pyrrolizidine‐1‐carboxlate (III). Retronecine (II') was 3 H labelled at the 1 methyl proton by the reduction of III with LiAl 3 H 4 . The semi‐synthetic pyrrolizidine alkaloid disenecioyl retronecine (Di‐3,3‐dimethylacrylic acid ester of retronecine). having a high specific activity. was prepared by the acylation of 3 H retronecine (II') with senecioyl chloride (3,3‐dimethylacryloyl chloride).