Macrocyclic pyrrolizidine alkaloids. Synthesis and stereochemistry of (+)-dicrotaline (13β-hydroxy-13α-methyl-1,2-didehydrocrotalanine) and (+)-13-epi-dicrotaline
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1819-1824
- https://doi.org/10.1039/p19830001819
Abstract
Treatment of (+)-retronecine (1) with the trimethylsilyl ether of 3-hydroxy-3-methylglutaric anhydride gave a mixture of the 7- and 9-monoesters of (+)-retronecine (1). Lactonisation of this mixture was achieved using the corresponding pyridine-2-thiol esters to give (+)-dicrotaline (13β-hydroxy-13α-methyl-1,2-didehydrocrotalanine)(2) and (+)-13-epi-dicrotaline (3). The absolute configuration at C-13 in both compounds was established by a sequence of selective reactions on each epimer to yield optically active mevalonolactone.This publication has 1 reference indexed in Scilit:
- Pyrrolizidine alkaloid biosynthesis. Incorporation of 14C-labelled precursors into retronecineJournal of the Chemical Society, Perkin Transactions 1, 1981