Synthesis of tritiated senecioyl dehydroretronecine, a pyrrolizidine alkaloid pyrrole

✍ Scribed by R. C. Shumaker; M.-T. S. Hsia; J. L. Seymour; J. R. Allen

• Book ID: 102371678
• Publisher: John Wiley and Sons
• Year: 1978
• Tongue: French
• Weight: 216 KB
• Volume: 15
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580150129

✦ Synopsis

T r i t i a t e d mono-and disenecioyl dehydroretronecine (3.3dimethyl -acryl i c acid esters o f 1 -hydroxymethyl-70-hydroxy-6,7dihydro-5H-pyrrol izine) ( I V and V) were prepared by acylation o f 9-H -dehydroretronecine (l-hydroxymethyl-7B-hydroxy-6.7dihydro-5H-pyrrolizine ( 111)). The synthesis o f dehydroretronecine involved a new, higher y i e l d method f o r preparing retronecinal (l-fonny1-70-hydroxy-6,7-dihydro-5H-pyrrol i z i n e ) (11) using p y r o l i t i c a l l y prepared activated Mn02.