1283712-97-9Relevant academic research and scientific papers
Studies on transannulation reactions across a nine-membered ring: The synthesis of natural product-like structures
Iqbal, Mudassar,Black, Richard J. G.,Winn, Joby,Reeder, Andrew T.,Blake, Alexander J.,Clarke, Paul A.
, p. 5062 - 5078 (2011/08/21)
A series of diverse natural product-like structures have been synthesised by the use of a number of novel transannulation reactions across a cyclononene ring. Transannular cyclisations through oxygen functionality have generated a number of bicyclo[5.3.1]systems containing bridged cyclic ethers and bicyclo[5.2.2]lactones, as well as a tetrahydrofuran-containing bridged analogue of hexacyclinic acid. An unprecedented Bronsted acid mediated transannular cyclisation between proximal carbons generated bicyclo[4.3.0] nonanes which form the core of the pinguisane and austrodorane families of sesquiterpenoids. In all cases the key factor that determined the mode of reactivity was the conformation of the nine-membered ring and the distance between the reacting centres. The Royal Society of Chemistry 2011.
Synthesis of an austrodorane sesquiterpenoid core via a transannular Prins cyclization
Clarke, Paul A.,Winn, Joby
, p. 1469 - 1472 (2011/06/10)
The bicyclo[4.3.0]nonane core of the austrodorane family of sesquiterpenoids has been synthesized via a novel transannular Prins cyclization. This strategy formed the fused 5,6-ring system and installed the required quaternary stereocentre at the ring fus
