4.8 Article

Total Synthesis of Huperzine R

Journal

ORGANIC LETTERS
Volume 20, Issue 1, Pages 119-121

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03555

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Funding

  1. JSPS KAKENHI [26713001, 16H01141, 17H01523]
  2. Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research
  3. BINDS) from the Japan Agency for Medical Research and Development (AMED)
  4. Grants-in-Aid for Scientific Research [16H01141, 17H01523] Funding Source: KAKEN

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A total synthesis of huperzine R was accomplished. Intramolecular cycloaddition of a nitrile oxide and reductive cleavage of the resulting isoxazoline induced Me sequential cleavage of the C-C and C-O bonds to form the characteristic bicyclic lactam core with an enone moiety. Construction of the butenolide moiety from the enone afforded huperzine R.

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