"In Water": Organocatalyzed Diastereoselective Multicomponent Reactions toward 2-Azapyrrolizidine Alkaloid Scaffolds

ACS Comb Sci. 2017 Jul 10;19(7):455-463. doi: 10.1021/acscombsci.7b00038. Epub 2017 Jun 20.

Abstract

Synthesis of the 2-aza analogues of pyrrolizidine and spirooxindole-2-azapyrrolizidine hybrid, a spiro-tetracyclic scaffold possessing multiple contiguous stereocenters, by an exclusive regio-, chemo-, and diastereoselective multicomponent reaction in water is reported. This logical and didactical tactic has integrated the principles of an ideal organic synthesis, privileged substructure-based diversity-oriented synthesis, and biology-oriented synthesis to access hybrid heterocyclic scaffolds.

Keywords: azapyrrolizidine and small molecules; diversity-oriented synthesis; multicomponent reaction; water.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Pyrrolizidine Alkaloids / chemical synthesis*
  • Solubility
  • Stereoisomerism
  • Water / chemistry*

Substances

  • Aza Compounds
  • Pyrrolizidine Alkaloids
  • Water