Journal of the Chemical Society. Perkin transactions I p. 1169 - 1172 (1988)
Update date:2022-07-30
Topics:
Barbour, Robert H.
Robins, David J.
Reaction of 2,3-bis(hydroxymethyl)-1-methyl-2,5-dihydropyrrole<(+/-)-synthanecine A> (3) with thionyl chloride produces (+/-)-3-chloromethyl-2-hydroxymethyl-1-methyl-2,5-dihydropyrrolium chloride (11), which was treated with a series of anhydrides and base at room temperature to give the corresponding 6-monoesters of (+/-)-synthanecine A.Intramolecular nucleophilic substitution of the chlorine by carboxylate anion in the presence of base (DBU) gives the corresponding macrocyclic diesters of (+/-)-synthanecine A.The pyrrolizidine alkaloid analogues <(6), (7), and (16)-(20)> are prepared in better yields than using Corey-Nicolaou lactonisation conditions.A range of new 10-membered <(8)-(10) and (12)-(14)> and 11-membered <(15) and (21)> macrocyclic diesters of (+/-)-synthanecine A has been prepared.
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(1988)
