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Synthesis of tritiated senecioyl dehydroretronecine, a pyrrolizidine alkaloid pyrrole
Author(s) -
Shumaker R. C.,
Hsia M.T. S.,
Seymour J. L.,
Allen J. R.
Publication year - 1978
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580150129
Subject(s) - chemistry , acylation , pyrrole , hydroxymethyl , yield (engineering) , pyrrolizidine , alkaloid , organic chemistry , stereochemistry , catalysis , materials science , metallurgy
Tritiated mono‐ and disenecioyl dehydroretronecine (3,3‐dimethyl‐acrylic acid esters of 1‐hydroxymethyl‐7β‐hydroxy‐6,7‐dihydro‐5H‐pyrrolizine) (IV and V) were prepared by acylation of 9‐H 3 ‐dehydroretronecine (1‐hydroxymethyl‐7β‐hydroxy‐6,7‐dihydro‐5H‐pyrrolizine (III)). The synthesis of dehydroretronecine involved a new, higher yield method for preparing retronecinal (1‐formyl‐7β‐hydroxy‐6,7‐dihydro‐5H‐pyrrolizine) (II) using pyrolitically prepared activated MnO 2 .