4.8 Article

Total Syntheses of Secalonic Acids A and D

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 12, Pages 3107-3110

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201311260

Keywords

dimerization; kinetic resolution; natural products; stannanes; total synthesis

Funding

  1. NIH [GM-099920, GM-067041]
  2. Vertex Pharmaceuticals, Inc.

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Total syntheses of the dimeric tetrahydroxanthone natural products secalonic acidsA and D are described. Key steps involve kinetic resolution of the tetrahydroxanthone core structure using homobenzotetramisole catalysis and late-stage copper(I)-mediated homodimerization of complex aryl stannane monomers.

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