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Accepted version

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2009

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/48632

Stereoselective Synthesis of (-)-Spicigerolide

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http://dx.doi.org/10.1021/jo8025753

Abstract

(-)-Spicigerolide was enantioselectively synthesized from a protected (S)-lactaldehyde. The synthesis of the polyacetylated framework relied on two Zn-mediated stereoselective additions of alkynes to aldehydes as well as a regiocontrolled [3,3]-sigmatropic rearrangement of an allylic acetate. The pyranone moiety was constructed via ring-closing metathesis.

Subject

Plantes, Botànica mèdica, Citotoxicitat per mediació cel·lular, Càncer, Estereoquímica, Productes naturals, Síntesi orgànica

Subject (English)

Plants, Medical botany, Cell-mediated cytotoxicity, Cancer, Stereochemistry, Natural products, Organic synthesis

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

GEORGES, Yohan, ARIZA PIQUER, Xavier and GARCÍA GÓMEZ, Jordi. Stereoselective Synthesis of (-)-Spicigerolide. Journal of Organic Chemistry. 2009. Vol. 74, num. 5, pags. 2008-2012. ISSN 0022-3263. [consulted: 6 of June of 2026]. Available at: https://hdl.handle.net/2445/48632

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