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

Validated

WOS: 16 ()

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.

OXFORD

0040-4020

10.1016/j.tet.2012.10.083