4.5 Article

Nickel-Promoted Reductive Cyclization Cascade: A Short Synthesis of a New Aromatic Strigolactone Analogue

Journal

SYNTHESIS-STUTTGART
Volume 49, Issue 16, Pages 3576-3581

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588804

Keywords

nickel; reductive coupling; stereospecific; cascade; synthesis

Funding

  1. National Natural Science Foundation of China [21472075]
  2. Ministry of Education of China [PCSIRT-15R28, lzujbky-2016-51, lzujbky-2016-ct02]

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A stereospecific synthesis of the tetrahydro-2H-indeno[1,2-b]furan skeleton, which is embedded in bioactive aromatic strigolactones such as GR24, is realized by a nickel-mediated tandem cross-coupling for the first time. The observed cis-stereoselectivity during the intramolecular formation of the Csp(3)-Csp(2) bond is rationalized through conformation analysis and DFT calculations.

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