4.8 Article

A Diastereodivergent Synthetic Strategy for the Syntheses of Communesin F and Perophoramidine

Journal

ORGANIC LETTERS
Volume 16, Issue 12, Pages 3316-3319

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5013263

Keywords

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Funding

  1. NIH-NIGMS [R01GM080269]
  2. Amgen
  3. Gordon and Betty Moore Foundation
  4. Caltech
  5. Fulbright (Foreign Student Program) [15111120]
  6. Ilju Foundation of Education Culture
  7. German Academic Exchange Service (DAAD)
  8. California TRDRP [14FT-0002]
  9. Bristol-Myers Squibb
  10. Swiss National Science Foundation

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An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations.

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