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Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon. | LitMetric
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Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon.

Takahiro Suzuki Hiroshi Okuyama Atsuhiro Takano Shinya Suzuki Isao Shimizu Susumu Kobayashi

J Org Chem

Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.

Published: March 2014

The synthesis of a novel hydrocarbon, dibarrelane, has been accomplished in 11 steps via an intramolecular REDDA reaction of a masked o-benzoquinone, followed by Clemmensen reduction and Barton decarboxylation. The twisted structure of the tetracyclic dibarrelane skeleton was also clarified via X-ray crystallography. Finally, it was proposed that dibarrelane has C2 symmetry rather than C(2v) symmetry.

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http://dx.doi.org/10.1021/jo5003455DOI Listing

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