Synlett 2023; 34(03): 271-276
DOI: 10.1055/a-1967-1284
letter

Total Synthesis and Structural Revision of Cephalosporolide J

,
Kazuo Kamaike
,


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Abstract

Herein, we report the first total synthesis of cephalosporolide J, which is a deep sea sediment derived polyketide harboring a unique bicyclo[3.3.0]furanolactone moiety. The adopted synthetic strategy consisted of the alkynylation of γ-lactone with lithium alkynyltrifluoroborate followed by a spiroketalization triggered by hydrogenation of the triple bond. Through this synthesis, the correct structure of cephalosporolide J is shown to be that of the 9-epi stereoisomer of the structure originally proposed.

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Publikationsverlauf

Eingereicht: 06. Oktober 2022

Angenommen nach Revision: 24. Oktober 2022

Accepted Manuscript online:
24. Oktober 2022

Artikel online veröffentlicht:
23. November 2022

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