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A straightforward route to functionalized trans-Diels-Alder motifs.

ABSTRACT: A sequence consisting of a Lewis acid-catalyzed Diels-Alder reaction on a 2-halocyclohexenone, followed by reductive alkylation, provides a route to trans-fused octalinones bearing angular methyl groups with functionality corresponding to that which would have been possible from a trans-directed Diels-Alder reaction.

SUBMITTER: Lee JH

PROVIDER: S-EPMC2974171 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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A straightforward route to functionalized trans-Diels-Alder motifs.

Lee Jun Hee JH Zhang Yandong Y Danishefsky Samuel J SJ

Journal of the American Chemical Society 20101001 41

A sequence consisting of a Lewis acid-catalyzed Diels-Alder reaction on a 2-halocyclohexenone, followed by reductive alkylation, provides a route to trans-fused octalinones bearing angular methyl groups with functionality corresponding to that which would have been possible from a trans-directed Diels-Alder reaction. ...[more]

PMID: 20863105

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