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2019-03-18

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cc-by (c) Guignard, Guillaume Michel Pablo et al., 2019
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/162614

Enantioselective synthesis of the ethyl analog of the marine alkaloid haliclorensin C

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https://doi.org/10.3390/molecules24061069

Abstract

The enantioselective synthesis (3.7% overall yield in nine steps from 2) and biological screening of the ethyl analog of the macrocyclic marine alkaloid haliclorensin C (compound 5) are reported. Amino alcohol 3, generated by a LiNH2BH3-promoted reductive ring-opening/debenzylation sequence from phenylglycinol-derived lactam 2, was used as the starting chiral linear building block. Incorporation of the undecene chain via the nosyl derivative 12, methylenation of the pentanol moiety, and a ring-closing metathesis are the key steps of the synthesis.

Subject

Alcaloides, Síntesi orgànica, Compostos macrocíclics

Subject (English)

Alkaloids, Organic synthesis, Macrocyclic compounds

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citation

GUIGNARD, Guillaume Michel Pablo, et al. Enantioselective synthesis of the ethyl analog of the marine alkaloid haliclorensin C. Molecules. 2019. Vol. 24, num. 6, pags. 1069-1077. ISSN 1420-3049. [consulted: 16 of August of 2026]. Available at: https://hdl.handle.net/2445/162614

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