4.7 Article

Toward the Synthesis of Paspaline-Type Indole-Terpenes: Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 14, Pages 9802-9810

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01193

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Funding

  1. Japanese Society for the Promotion of Science (JSPS)/the Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan [20H02867]
  2. Sumitomo foundation
  3. Naito foundation
  4. Grants-in-Aid for Scientific Research [20H02867] Funding Source: KAKEN

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The core scaffold of paspaline-type indole-terpenes was synthesized using the House-Meinwald rearrangement as a key step, successfully constructing contiguous asymmetric quaternary carbon centers.
The core scaffold of paspaline-type indole-terpenes was synthesized by using the House-Meinwald rearrangement as a key step. Rearrangement of the epoxide methyl group in the precursor with methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) as a Lewis acid proceeded smoothly to construct contiguous asymmetric quaternary carbon centers by a 1,2-chirality transfer.

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