Further Studies on Quinone Diels-Alder Reactions with 1,3,3-Trimethyl-2-vinylcyclohexenes: Regioselective Synthesis of 12-Methyl-podocarpane Diterpenes and Isolation of a Hetero Diels-Alder Product from 1,4-Benzoquinone

Thomas A. Engler Department of Chemistry, University of Kansas, Lawrence, KS, 66045, USA

UmaShanker Sampath Department of Chemistry, University of Kansas, Lawrence, KS, 66045, USA

David Vander Velde Department of Chemistry, University of Kansas, Lawrence, KS, 66045, USA

Fusao Takusagawa Department of Chemistry, University of Kansas, Lawrence, KS, 66045, USA

Abstract

Diels-Alder reactions of 2-[(E)-β-alkoxyvinyl]-1,3,3-trimethyl-cyclohexenes with 2-methoxy-3-methyl-1,4-benzoquinone regioselectively produce adducts possessing the 12-methyl-podocarpane ring skeleton. In addition, in the reaction with 1,4-benzoquinone an unusual hetero Diels-Alder product involving the C[dbnd]O group of the quinone is found in low yield.

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Further Studies on Quinone Diels-Alder Reactions with 1,3,3-Trimethyl-2-vinylcyclohexenes: Regioselective Synthesis of 12-Methyl-podocarpane Diterpenes and Isolation of a Hetero Diels-Alder Product from 1,4-Benzoquinone

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Further Studies on Quinone Diels-Alder Reactions with 1,3,3-Trimethyl-2-vinylcyclohexenes: Regioselective Synthesis of 12-Methyl-podocarpane Diterpenes and Isolation of a Hetero Diels-Alder Product from 1,4-Benzoquinone

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