Total Synthesis of (-)-Isoschizogamine

Chemistry. 2015 Nov 9;21(46):16400-3. doi: 10.1002/chem.201503606. Epub 2015 Oct 1.

Abstract

The total synthesis of (-)-isoschizogamine was accomplished, featuring the construction of the quaternary carbon center by the modified Johnson-Claisen rearrangement in basic media and the facile assembly of the key tetracyclic quinolone intermediate through a cascade cyclization. The characteristic cyclic aminal was constructed by late-stage C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4 NIO4 and subsequent Bi(OTf)3 -mediated cyclization.

Keywords: CH functionalization; alkaloids; aminal; cascade reaction; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Hydrogen Bonding
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Mesylates / chemistry
  • Onium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • Mesylates
  • Onium Compounds
  • isoschizogamine
  • Bi(OTf)3