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Further Investigation of the Intermolecular Diels-Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids.

ABSTRACT: The convergent synthesis of bicyclo[2.2.2]diazaoctane structures using an intermolecular Diels-Alder cycloaddition between a pyrazinone and commercially available fumarate or maleate precursors is reported. High reactivity and stereoselection is observed with both dienophile substrates. Structure validation was achieved by conversion of cycloadducts into known [2.2.2]diazabicyclic compounds or into crystalline derivatives suitable for X-ray analysis. The cycloadduct derived from reaction of pyrazinone and maleic anhydride underwent selective anhydride ring opening and intersected an established precursor in the synthesis of brevianamide B.

SUBMITTER: Perkins JC

PROVIDER: S-EPMC6613383 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Further Investigation of the Intermolecular Diels-Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids.

Perkins Jonathan C JC Wang Xiye X Pike Robert D RD Scheerer Jonathan R JR

The Journal of organic chemistry 20171127 24

The convergent synthesis of bicyclo[2.2.2]diazaoctane structures using an intermolecular Diels-Alder cycloaddition between a pyrazinone and commercially available fumarate or maleate precursors is reported. High reactivity and stereoselection is observed with both dienophile substrates. Structure validation was achieved by conversion of cycloadducts into known [2.2.2]diazabicyclic compounds or into crystalline derivatives suitable for X-ray analysis. The cycloadduct derived from reaction of pyra ...[more]

PMID: 29172511

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