Studies on transannulation reactions across a nine-membered ring: the synthesis of natural product-like structures
- Resource Type
- Authors
- Andrew T. Reeder; Richard J. G. Black; Mudassar Iqbal; Paul A. Clarke; Joby Winn; Alexander J. Blake
- Source
- Organic & Biomolecular Chemistry. 9:5062
- Subject
- Models, Molecular
Natural product
Bicyclic molecule
Stereochemistry
Organic Chemistry
Molecular Conformation
Cycloparaffins
Stereoisomerism
Hexacyclinic acid
Crystallography, X-Ray
Ring (chemistry)
Biochemistry
Bridged Bicyclo Compounds
chemistry.chemical_compound
Cyclononene
chemistry
Cyclization
Reactivity (chemistry)
Physical and Theoretical Chemistry
Brønsted–Lowry acid–base theory
- Language
- ISSN
- 1477-0539
1477-0520
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.