Total Synthesis of (+)-Pancratistatin by the Rh(III)-Catalyzed Addition of a Densely Functionalized Benzamide to a Sugar-Derived Nitroalkene

Org Lett. 2017 Jun 2;19(11):2985-2988. doi: 10.1021/acs.orglett.7b01220. Epub 2017 May 24.

Abstract

Herein, we report the concise total synthesis of (+)-pancratistatin, accessed in a 10-step linear sequence from commercially available inputs. The convergent synthesis features a highly diastereoselective Rh(III)-catalyzed C-H bond addition to a d-glucose-derived nitroalkene and a late-stage intramolecular transamidation to furnish the B ring lactam.

Publication types

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

MeSH terms

  • Alkenes
  • Amaryllidaceae Alkaloids / chemistry*
  • Benzamides
  • Catalysis
  • Isoquinolines / chemistry*
  • Molecular Structure
  • Nitro Compounds
  • Rhodium
  • Sugars

Substances

  • Alkenes
  • Amaryllidaceae Alkaloids
  • Benzamides
  • Isoquinolines
  • Nitro Compounds
  • Sugars
  • pancratistatin
  • Rhodium