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Published September 13, 2000 | Supplemental Material
Journal Article Open

Enantioselective Synthesis of the Cyclopentyl Core of the Axinellamines

Abstract

Axinellamines A−D (1−4) are novel bis-guanidine alkaloids isolated from the marine sponge Axinella sp. of which Axinellamines B−D (2−4) have been shown to possess bactericidal activity against Helicobacter pylori, a bacterium implicated in pepticular and gastric cancer.1 These natural products are noteworthy for the structural complexity of the polycyclic framework incorporating fused and spirocyclic ring systems. Moreover, embedded within these structures is a stereochemically complex and densely functionalized cyclopentyl core that presents a daunting synthetic challenge. A similarly substituted cyclopentane core can be found in palau'amine 5 which critically differs from that of 1−4 in the relative stereochemical relationships of the pendant functionality.2 Palau'amine 5 has attracted considerable attention due to its potent antibiotic, immunosuppressive, and cytotoxic properties (Chart 1).

Additional Information

© 2000 American Chemical Society. Received 5 June 2000. Published online 26 August 2000. Published in print 1 September 2000. We thank Professor Volker Gramlich of the ETH-Z Laboratory of Crystallography for X-ray crystallographic analyses on compound 16. We thank the National Science Foundation for a pre-doctoral fellowship for J.T.S. This research has been supported by an award from the Packard Foundation, Swiss National Science Foundation, as well as generous support from Merck, Astra-Zeneca, and Hoffman LaRoche.

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