Pyrrolizidine alkaloid analogues. Synthesis of eleven-membered macrocyclic diesters of retronecine
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 1117-1121
- https://doi.org/10.1039/p19820001117
Abstract
Treatment of (+)-retronecine (1) with 3,3-disubstituted glutaric anhydride derivatives (2) yielded mixtures of the retronecine 7- and 9-monoesters, which were assayed by 1H n.m.r, spectrometry. Lactonisation of these mixtures was achieved by the Corey–Nicolaou method to give a range of eleven-membered macrocyclic pyrrolizidine diesters (5) with different substituents at C-13. The macrocyclic nature of these pyrrolizidine alkaloid analogues was established by comparison of their 1H n.m.r. and mass spectra with those of natural pyrrolizidine alkaloids.This publication has 4 references indexed in Scilit:
- Relation of structural features to pyrrolic metabolites in livers of rats given pyrrolizidine alkaloids and derivativesChemico-Biological Interactions, 1981
- Synthesis of crobarbatine acetate. A macrocyclic pyrrolizidine alkaloid esterJournal of the American Chemical Society, 1981
- Pyrrolizidine alkaloid biosynthesis. Incorporation of 14C-labelled precursors into retronecineJournal of the Chemical Society, Perkin Transactions 1, 1981
- Synthesis of macrolidesTetrahedron, 1977