Total Synthesis of Polysubstituted γ-Butyrolactone Lignans (-)-Hinokinin, (-)-Bicubebin B, and (-)-Isodeoxypodophyllotoxin via Oxime Carbonate Formation

Org Lett. 2023 Jan 13;25(1):31-36. doi: 10.1021/acs.orglett.2c03727. Epub 2022 Dec 23.

Abstract

The diverse structures and profound biological activities of lignan natural products have enticed significant effort in the exploration of new methodologies for their total synthesis. We have prepared γ-butyrolactone oximes from readily available δ-nitro alcohols via Boc2O mediated cyclization. The mild conditions are compatible with a wide range of functional groups, and this methodology has been applied to the total synthesis of five lignan natural products.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • 4-Butyrolactone / chemistry
  • Biological Products*
  • Lignans* / chemistry

Substances

  • 4-Butyrolactone
  • Biological Products
  • deoxypodophyllotoxin
  • hinokinin
  • Lignans
  • bicubebin B