Diversity-Oriented Approaches to Polycyclics and Bioinspired Molecules via the Diels-Alder Strategy: Green Chemistry, Synthetic Economy, and Beyond

ACS Comb Sci. 2015 May 11;17(5):253-302. doi: 10.1021/co500146u. Epub 2015 Apr 23.

Abstract

We describe diverse approaches to various dienes and their utilization in the Diels-Alder reaction to produce a variety of polycycles. The dienes covered here are prepared by simple alkylation reaction or via the Claisen rearrangement or by enyne metathesis of alkyne or enyne building blocks. Here, we have also included the Diels-Alder chemistry of dendralenes, a higher analog of cross-conjugated dienes. The present article is inclusive of o-xylylene derivatives that are generated in situ starting with benzosultine or benzosulfone derivatives. The Diels-Alder reaction of these dienes with various dienophiles gave diverse polycyclic systems and biologically important targets.

Keywords: Diels−Alder reaction; amino acids; dienes; diversity-oriented synthesis; green chemistry; polycyclics.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Cycloaddition Reaction*
  • Green Chemistry Technology*
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry

Substances

  • Alkadienes
  • Polycyclic Compounds