Total Synthesis of (±)-Phomoidride D

Joyce C. Leung, Aaron A. Bedermann, Jon 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

5 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Cycloaddition
Cyclization
Oxidation
phomoidride D

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Leung, J. C., Bedermann, A. A., Njardarson, J. T., Spiegel, D. A., Murphy, G. K., Hama, N., ... Wood, J. L. (2018). Total Synthesis of (±)-Phomoidride D. Angewandte Chemie - International Edition, 57(7), 1991-1994. https://doi.org/10.1002/anie.201712369

Total Synthesis of (±)-Phomoidride D. / Leung, Joyce C.; Bedermann, Aaron A.; Njardarson, Jon T; Spiegel, David A.; Murphy, Graham K.; Hama, Naoto; Twenter, Barry M.; Dong, Ping; Shirahata, Tatsuya; McDonald, Ivar M.; Inoue, Munenori; Taniguchi, Nobuaki; McMahon, Travis C.; Schneider, Christopher M.; Tao, Nancy; Stoltz, Brian M.; Wood, John L.

In: Angewandte Chemie - International Edition, Vol. 57, No. 7, 12.02.2018, p. 1991-1994.

Research output: Contribution to journalArticle

Leung, JC, Bedermann, AA, Njardarson, JT, Spiegel, DA, Murphy, GK, Hama, N, Twenter, BM, Dong, P, Shirahata, T, McDonald, IM, Inoue, M, Taniguchi, N, McMahon, TC, Schneider, CM, Tao, N, Stoltz, BM & Wood, JL 2018, 'Total Synthesis of (±)-Phomoidride D', Angewandte Chemie - International Edition, vol. 57, no. 7, pp. 1991-1994. https://doi.org/10.1002/anie.201712369
Leung JC, Bedermann AA, Njardarson JT, Spiegel DA, Murphy GK, Hama N et al. Total Synthesis of (±)-Phomoidride D. Angewandte Chemie - International Edition. 2018 Feb 12;57(7):1991-1994. https://doi.org/10.1002/anie.201712369
Leung, Joyce C. ; Bedermann, Aaron A. ; Njardarson, Jon T ; Spiegel, David A. ; Murphy, Graham K. ; Hama, Naoto ; Twenter, Barry M. ; Dong, Ping ; Shirahata, Tatsuya ; McDonald, Ivar M. ; Inoue, Munenori ; Taniguchi, Nobuaki ; McMahon, Travis C. ; Schneider, Christopher M. ; Tao, Nancy ; Stoltz, Brian M. ; Wood, John L. / Total Synthesis of (±)-Phomoidride D. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 7. pp. 1991-1994.
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