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

ABSTRACT: 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.

SUBMITTER: Shin I

PROVIDER: S-EPMC5096380 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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

Shin Inji I Hong Suckchang S Krische Michael J MJ

Journal of the American Chemical Society 20161025 43

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. ...[more]

PMID: 27779393

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