Ansafurantrienins, Unprecedented Ansatrienin Derivatives Formed via Photocatalytic Intramolecular [3 + 2] Oxidative Cycloaddition

Ansafurantrienins A–H, bearing a unique 5/6/8 dihydrofuran-fused benzo­[b]­azocine chromophore, were isolated from Streptomyces flaveolus. Their structures, especially in the dihydrofuran unit, were unambiguously established by spectroscopic analyses, molecular modeling, and TDDFT/ECD calculations....

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Published inOrganic letters Vol. 24; no. 2; pp. 592 - 596
Main Authors Li, Hongji, Chen, Shuo, Wang, Jinxin, Zhang, Mengxue, Wu, Wenhui, Liu, Wen, Sun, Peng
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.01.2022
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Summary:Ansafurantrienins A–H, bearing a unique 5/6/8 dihydrofuran-fused benzo­[b]­azocine chromophore, were isolated from Streptomyces flaveolus. Their structures, especially in the dihydrofuran unit, were unambiguously established by spectroscopic analyses, molecular modeling, and TDDFT/ECD calculations. The ansafurantrienins were proposed to be generated via intramolecular [3 + 2] oxidative cycloaddition, which was achieved by photocatalytic reaction with UV light and oxygen and found to have solvent-dependent stereoselectivity. Ansafurantrienins showed significant antiproliferative effects against pancreatic cancer cells. The results led to a structural revision of strecacansamycins.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04032