Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C–C Bond Formation

Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C–C Bond Formation

Diverse hydrogen-mediated C–C couplings enable construction of the actin-binding marine polyketide swinholide A in only 15 steps (longest linear sequence), roughly half the steps required in two prior total syntheses. The redox-economy, chemo- and stereo­selectivity embodied by this new class of C–C...

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Veröffentlicht in:Journal of the American Chemical Society 2016-11, Vol.138 (43), p.14246-14249
Hauptverfasser: Shin, Inji, Hong, Suckchang, Krische, Michael J
Format: Artikel
Sprache:eng
Schlagworte:
Carbon - chemistry
Chemistry Techniques, Synthetic
Hydrogen - chemistry
Marine Toxins - chemical synthesis
Marine Toxins - chemistry
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Zusammenfassung:Diverse hydrogen-mediated C–C couplings enable construction of the actin-binding marine polyketide swinholide A in only 15 steps (longest linear sequence), roughly half the steps required in two prior total syntheses. The redox-economy, chemo- and stereo­selectivity embodied by this new class of C–C couplings are shown to evoke a step-change in efficiency.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b10645