Marine organisms have been known to be a source of polyacetylenic compounds which have shown biological effects ranging from anti-inflammatory to anticancer activity.  Callyspongamide A, a long, linear polyacetylenic amide, was extracted from Callyspongia fistularis, found in the Red Sea. Less than three milligrams were isolated, which was enough only for structural elucidation and biological testing against HeLa cancer cells. Despite its moderate cytotoxicity against HeLa cells our research group became interested in testing Callyspongamide A against different cancer cell lines and search for other possible biological activities of this unusual polyacetylenic amide. Extraction of significant quantities of Callyspongamide A from sponges is not practical, which makes the total synthesis of this natural compound the best alternative. Retrosynthetic analysis of its structure calls for the protection of a nine-carbon haloalkyl alcohol and a five-carbon acetylenic alcohol with different protecting groups, coupling of both moieties through lithium-mediated alkyne alkylation, sequential deprotection of one of the alcohols with subsequent oxidation to carboxylic acid and coupling to phenethylamine to finish one “half” of the molecule. Deprotection and controlled oxidation of the second alcohol to an aldehyde, followed by Stork-Zhao olefination and acetylene alkylation would yield Callyspongamide A. This presentation reports the current state of this total synthesis, where the intermediate monoprotected alkynol  14-((2-methoxyethoxy)methoxy)tetradec-4-yn-1-ol was synthesized with good yield and characterized through NMR spectrometry. Next steps involve the planned final synthetic reactions and establishment of the synthetic methodology for the preparation of analogs to explore structure-activity relationship.<br/>

Synthesis of an intermediate towards the total synthesis of the potential cytotoxic agent Callyspongamide A

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.