Bistellettazines A-C and bistellettazole A

new terpenyl-pyrrolizidine and terpenyl-imidazole alkaloids from a southern Australian marine sponge, Stelletta sp

Mohamed El-Naggar*, Andrew M. Piggott, Robert J. Capon

*Corresponding author for this work

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

(Chemical Equation Presented) Four new alkaloids have been isolated during chemical investigations into a southern Australian marine sponge, Stelletta p. Detailed spectroscopic analysis, supported by chemical degradation and partial synthesis, permitted structure elucidation of bistellettazines A-C (1-3), the first reported examples of terpenyl-pyrrolizidine conjugates, and bistellettazole A (4), a unique cyclic terpenyl-imidazole conjugate. The alkaloids 1-4 feature unprecedented carbon skeletons that are proposed to share a common convergent biosynthetic origin, arising via the biogenic equivalent of a Diels-Alder addition between two hypothetical polyenyl norsesquiterpene precursors.

Original languageEnglish
Pages (from-to)4247-4250
Number of pages4
JournalOrganic Letters
Volume10
Issue number19
DOIs
Publication statusPublished - 2008
Externally publishedYes

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