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

doi:10.1021/ol8016512

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 journal › Article

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 language	English
Pages (from-to)	4247-4250
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	19
DOIs	https://doi.org/10.1021/ol8016512
Publication status	Published - 2008
Externally published	Yes

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El-Naggar, M., Piggott, A. M., & Capon, R. J. (2008). Bistellettazines A-C and bistellettazole A: new terpenyl-pyrrolizidine and terpenyl-imidazole alkaloids from a southern Australian marine sponge, Stelletta sp. Organic Letters, 10(19), 4247-4250. https://doi.org/10.1021/ol8016512

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AB - (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.

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10.1021/ol8016512

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