Reversible cyclopropane ring-cleavage reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6]fenestratetraenes

Chemistry. 2012 Oct 22;18(43):13585-8. doi: 10.1002/chem.201202903. Epub 2012 Sep 17.

Abstract

Opening and closing a chemical window: oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Bridged-Ring Compounds / chemistry*
  • Cyclopropanes / chemistry*
  • Diterpenes / chemistry
  • Organometallic Compounds / chemistry
  • Oxidation-Reduction
  • Pyridinium Compounds / chemistry
  • Quantum Theory

Substances

  • Aza Compounds
  • Bridged-Ring Compounds
  • Cyclopropanes
  • Diterpenes
  • Organometallic Compounds
  • Pyridinium Compounds
  • aza(5.6.5.6)fenestratetrene
  • oxa-(5.6.5.6)fenestratetrene
  • salvileucalin B
  • cyclopropane
  • pyridinium chlorochromate
  • diisobutylaluminum