Stereoselective preparation of cyclobutanes with four different substituents: total synthesis and structural revision of pipercyclobutanamide A and piperchabamide G

Angew Chem Int Ed Engl. 2012 Jul 23;51(30):7503-6. doi: 10.1002/anie.201203379. Epub 2012 Jun 19.

Abstract

A general strategy was developed for the diastereo- and enantioselective synthesis of cyclobutanes with four different substituents. It consists of three transition metal-catalyzed reactions — a RhII-catalyzed cyclopropanation, a AgI-catalyzed regioselective and stereospecific ring expansion, and a RhI-catalyzed addition reaction. Structures of pipercyclobutanamide A and piperchabamide G were synthesized and revised.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Cyclobutanes / chemical synthesis
  • Cyclobutanes / chemistry*
  • Piper / chemistry*
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Amides
  • Biological Products
  • Cyclobutanes
  • Rhodium