Issue 14, 2011
From the journal:

Organic & Biomolecular Chemistry

Studies on transannulation reactions across a nine-membered ring: the synthesis of natural product-like structures†

Mudassar Iqbal,a   Richard J. G. Black,b   Joby Winn,a   Andrew T. Reeder,a   Alexander J. Blake‡b  and  Paul A. Clarke*ab  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, North Yorks, UK
E-mail: paul.clarke@york.ac.uk
Fax: +44 1904 322516
Tel: +44 1904 322614

b School of Chemistry, University of Nottingham, University Park, Nottingham, Notts, UK

Abstract

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 Brønsted 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.

Graphical abstract: Studies on transannulation reactions across a nine-membered ring: the synthesis of natural product-like structures

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Article information

DOI
https://doi.org/10.1039/C1OB05448A
Article type
Paper
Submitted
21 Mar 2011
Accepted
11 Apr 2011
First published
12 Apr 2011

Org. Biomol. Chem., 2011,9, 5062-5078

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Studies on transannulation reactions across a nine-membered ring: the synthesis of natural product-like structures

M. Iqbal, R. J. G. Black, J. Winn, A. T. Reeder, A. J. Blake and P. A. Clarke, Org. Biomol. Chem., 2011, 9, 5062 DOI: 10.1039/C1OB05448A

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