Synthesis of Substituted Bicyclo[2.2.2]octatrienes

Synthesis of Substituted Bicyclo[2.2.2]octatrienes

An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels−Alder reaction of this molecule with an activated acetylene, conversion of the diol to the...

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Veröffentlicht in:Journal of organic chemistry 1997-12, Vol.62 (26), p.9076-9082
Hauptverfasser: Wagaman, Michael W, Bellmann, Erika, Cucullu, Michèle, Grubbs, Robert H
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container_issue 26
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container_title Journal of organic chemistry
container_volume 62
creator Wagaman, Michael W
Bellmann, Erika
Cucullu, Michèle
Grubbs, Robert H
description An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels−Alder reaction of this molecule with an activated acetylene, conversion of the diol to the final olefin was accomplished through formation of a thiocarbonate intermediate and subsequent reaction with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (DPD). The synthesis developed allows a variety of barrelenes to be prepared in as few as three steps from commercially available starting materials.
doi_str_mv 10.1021/jo971039y
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title Synthesis of Substituted Bicyclo[2.2.2]octatrienes
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