✦ LIBER ✦

Synthesis of a tritium labelled pyrrolizidine alkaloidisenecioyl retronecine

✍ Scribed by I. C. Hsu; J. R. Allen

Book ID: 102370459
Publisher: John Wiley and Sons
Year: 1975
Tongue: French
Weight: 244 KB
Volume: 11
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2590110110

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✦ Synopsis

Abstract

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).

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