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Foley, DA,O'Leary, P,Buckley, NR,Lawrence, SE,Maguire, AR
2013
February
Tetrahedron
Synthetic approaches to the daucane sesquiterpene derivatives employing the intramolecular Buchner cyclisation of alpha-diazoketones
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RANEY-NICKEL CATALYST CAROTANE SESQUITERPENE TRICHODERMA-VIRENS ASYMMETRIC-SYNTHESIS ARYL DIAZOKETONES ORGANIC-SYNTHESIS AMINO-ACIDS ISOMERIZATION CONSTRUCTION EFFICIENT
69
1778
1794
The use of the intramolecular Buchner cyclisation of an alpha-diazoketone as an approach to the synthesis of daucane sesquiterpenes is described; in particular the synthesis of the cis-fused analogue of dihydro CAF-603. The key step in the synthesis is the intramolecular Buchner cyclisation, which provides the bicydo [5.3.0]decane framework with the required stereochemistry at the quaternary centre generated in the cyclisation. A synthetic route enabling access to an asymmetric synthesis is also outlined. (C) 2012 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tet.2012.10.083
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