4.4 Article

Synthetic Studies on Bilobalide

Journal

SYNLETT
Volume 31, Issue 3, Pages 290-294

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1691559

Keywords

desymmetrization; Diels-Alder reaction; Mukaiyama hydration; quaternary carbon; tertiary alcohol

Funding

  1. Japan Society for the Promotion of Science (JSPS KAKENHI) [JP17H01523]
  2. Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research
  3. BINDS) from Japan Agency for Medical Research and Development (AMED) [JP19am0101099]

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We disclose our synthetic studies on bilobalide, which features a Diels-Alder reaction of a cyclic anhydride to form two contiguous quaternary carbon centers, desymmetrization of a symmetric diol, and construction of a cyclic acetal under acidic conditions with inversion of configuration at an allylic position.

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