Total Synthesis of (-)-BastimolideâA: A Showcase for Type I Anion Relay Chemistry.

Cox, Joshua B; Kellum, Alex A; Zhang, Yiwen; Li, Bo; Smith, Amos B

Total Synthesis of (-)-BastimolideâA: A Showcase for Type I Anion Relay Chemistry.

Cox, Joshua B; Kellum, Alex A; Zhang, Yiwen; Li, Bo; Smith, Amos B.

Afiliación

Cox JB; Department of Chemistry, University of Pennsylvania, 231 S. 34th street, Philadelphia, PA 19104, USA.
Kellum AA; Department of Chemistry, University of Pennsylvania, 231 S. 34th street, Philadelphia, PA 19104, USA.
Zhang Y; Department of Chemistry, University of Pennsylvania, 231 S. 34th street, Philadelphia, PA 19104, USA.
Li B; Department of Chemistry, University of Pennsylvania, 231 S. 34th street, Philadelphia, PA 19104, USA.
Smith AB; Department of Chemistry, University of Pennsylvania, 231 S. 34th street, Philadelphia, PA 19104, USA.

Angew Chem Int Ed Engl ; 61(28): e202204884, 2022 07 11.

Article en En | MEDLINE | ID: mdl-35608327

RESUMEN

A highly convergent total synthesis of (-)-bastimolideâA (1), a polyhydroxy antimalarial macrolide, has been achieved via a longest linear sequence of twenty steps from commercially available glycidyl ethers. Type I Anion Relay Chemistry (ARC) coupling tactics enable rapid construction of the molecule's 1,5-polylol backbone. A late-stage B-alkyl Suzuki-Miyaura union and an Evans-modified Mukaiyama macrolactonization generate the forty-membered Z-α,ß-unsaturated macrocyclic lactone.

Asunto(s)

Antimaláricos; Macrólidos; Aniones; Lactonas; Estructura Molecular; Estereoisomerismo

Palabras clave

Antimalarial Agents; Macrolides; Multicomponent Coupling; Natural Products; Total Synthesis

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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Macrólidos / Antimaláricos Idioma: En Revista: Angew Chem Int Ed Engl Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos

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