Total Synthesis of (±)-Phomoidride D

Joyce C. Leung, Aaron A. Bedermann, Jón T. Njardarson, David A. Spiegel, Graham K. Murphy, Naoto Hama, Barry M. Twenter, Ping Dong, Tatsuya Shirahata, Ivar M. McDonald, Munenori Inoue, Nobuaki Taniguchi, Travis C. McMahon, Christopher M. Schneider, Nancy Tao, Brian M. Stoltz, John L. Wood

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI2-mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.

Original languageEnglish (US)
Pages (from-to)1991-1994
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number7
DOIs
StatePublished - Feb 12 2018

Keywords

  • bicyclic compounds
  • cycloaddition
  • natural products
  • oxidation
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Leung, J. C., Bedermann, A. A., Njardarson, J. T., Spiegel, D. A., Murphy, G. K., Hama, N., Twenter, B. M., Dong, P., Shirahata, T., McDonald, I. M., Inoue, M., Taniguchi, N., McMahon, T. C., Schneider, C. M., Tao, N., Stoltz, B. M., & Wood, J. L. (2018). Total Synthesis of (±)-Phomoidride D. Angewandte Chemie - International Edition, 57(7), 1991-1994. https://doi.org/10.1002/anie.201712369