Synthetic approaches to the daucane sesquiterpene derivatives employing the intramolecular Buchner cyclisation of α-diazoketones

…, P O'Leary, NR Buckley, SE Lawrence, AR Maguire

Index: Foley, David A.; O'Leary, Patrick; Buckley, N. Rachael; Lawrence, Simon E.; Maguire, Anita R. Tetrahedron, 2013 , vol. 69, # 6 p. 1778 - 1794

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Citation Number: 9

Abstract

The use of the intramolecular Buchner cyclisation of an α-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 bicyclo [5.3. 0] decane framework with the required stereochemistry at the quaternary centre generated in the cyclisation. A synthetic route ...