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Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative.

ABSTRACT: The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

SUBMITTER: Tabuchi T

PROVIDER: S-EPMC3629056 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative.

Tabuchi Toshiki T Urabe Daisuke D Inoue Masayuki M

Beilstein journal of organic chemistry 20130404

The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine. ...[more]

PMID: 23616810

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