97185-52-9Relevant academic research and scientific papers
Synthesis of Macrocyclic Pyrrolizidine Alkaloid Analogues from (-)-(7R,8R)-1-Chloromethyl-1,2-didehydro-7-hydroxypyrrolizidinium Chloride
Burton, Michael,Robins, David J.
, p. 585 - 590 (2007/10/02)
Treatment of the (-)-hydrochloride of (7R,8R)-1-chloromethyl-1,2-didehydro-7-hydroxypyrrolizidine (2) with a series of aromatic and unsaturated anhydrides at room temperature gave the corresponding macrocyclic diesters of retronecine (1).The reaction probably takes place by initial formation of the 7-monoesters of the allylic chloride (2), followed by intramolecular nucleophilic substitution of the chlorine by carboxylate anion.A range of ten-membered macrocyclic diesters of retronecine (1), and one example each of an 11-membered, (13), and 12-membered pyrrolizidine alkaloid analogue, (14), have been prepared.
