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Enantioselective Synthesis of the Cyclopentyl Core of the Axinellamines

Starr, Jeremy T. and Koch, Guido and Carreira, Erick M. (2000) Enantioselective Synthesis of the Cyclopentyl Core of the Axinellamines. Journal of the American Chemical Society, 122 (36). pp. 8793-8794. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170411-152927665

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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).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja0019575DOIArticle
http://pubs.acs.org/doi/full/10.1021/ja0019575PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja0019575PublisherSupporting Information
ORCID:
AuthorORCID
Carreira, Erick M.0000-0003-1472-490X
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.
Funders:
Funding AgencyGrant Number
David and Lucile Packard FoundationUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
MerckUNSPECIFIED
AstraZenecaUNSPECIFIED
Hoffmann-La RocheUNSPECIFIED
Issue or Number:36
Record Number:CaltechAUTHORS:20170411-152927665
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170411-152927665
Official Citation:Enantioselective Synthesis of the Cyclopentyl Core of the Axinellamines Jeremy T. Starr, Guido Koch, and Erick M. Carreira Journal of the American Chemical Society 2000 122 (36), 8793-8794 DOI: 10.1021/ja0019575
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76522
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:12 Apr 2017 16:03
Last Modified:09 Mar 2020 13:18

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