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Issue 5, 2010
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A tangled web—interconnecting pathways to amorphadiene and the amorphene sesquiterpenes

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Abstract

Quantum chemical studies on the formation of amorphadiene and the amorphene sesquiterpenes are described. These natural products are commonly thought to arise from distinct pathways involving initial 1,6- and 1,10-cyclization of farnesyl diphosphate, respectively. We have found, using density functional calculations, that the pathway usually invoked for amorphadiene formation is not only energetically feasible, but is also the energetically favored pathway to the amorphenes as a result of a low energy (two-step) 1,5-hydride transfer involving an unusual carbocation containing a 3-center 2-electron [C⋯H⋯C]+ bonding array.

Graphical abstract: A tangled web—interconnecting pathways to amorphadiene and the amorphene sesquiterpenes

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Publication details

The article was received on 12 Jun 2010, accepted on 12 Jul 2010 and first published on 13 Aug 2010


Article type: Edge Article
DOI: 10.1039/C0SC00333F
Citation: Chem. Sci., 2010,1, 609-614
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    A tangled web—interconnecting pathways to amorphadiene and the amorphene sesquiterpenes

    Y. J. Hong and D. J. Tantillo, Chem. Sci., 2010, 1, 609
    DOI: 10.1039/C0SC00333F

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