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

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2017 Nov 28

PMID 29172511

Citations 2

Authors

Jonathan C Perkins

Xiye Wang

Robert D Pike

Jonathan R Scheerer

Affiliations

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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.

Citing Articles

Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis.

Godfrey R, Jones H, Green N, Lawrence A Chem Sci. 2022; 13(5):1313-1322.

PMID: 35222915 PMC: 8809396. DOI: 10.1039/d1sc05801k.

Total synthesis of brevianamide A.

Godfrey R, Green N, Nichol G, Lawrence A Nat Chem. 2020; 12(7):615-619.

PMID: 32284576 DOI: 10.1038/s41557-020-0442-3.

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