Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues

J Org Chem. 2017 Dec 1;82(23):12840-12848. doi: 10.1021/acs.joc.7b02178. Epub 2017 Nov 7.

Abstract

A domino reaction with the organocatalytic enantioselective Michael-acetalization-Henry reaction of 2-hydroxynitrostyrene and 5-oxohexanal was developed for the synthesis of hexahydro-6H-benzo[c]chromenones with four consecutive stereogenic centers and high enantioselectivity (up to >99% ee). The transformation of a NaBH4-reduced adduct to the aflatoxin system via the Nef-cyclization process was achieved by the assistant of ZnBr2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Aflatoxins / chemistry*
  • Catalysis
  • Chromones / chemistry*
  • Hydroxy Acids / chemistry*
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Organic Chemicals
  • Stereoisomerism
  • Styrene / chemistry*

Substances

  • Acetals
  • Aflatoxins
  • Chromones
  • Hydroxy Acids
  • Nitro Compounds
  • Organic Chemicals
  • Styrene