Synthesis of the Madangamine Alkaloid Core by a C-C Bond Activation Cascade

Matthew S. Eastwood; Christopher J. Douglas

doi:10.1021/acs.orglett.9b02331

Synthesis of the Madangamine Alkaloid Core by a C-C Bond Activation Cascade

Matthew S. Eastwood, Christopher J. Douglas

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The diazatricyclic core of the madangamine alkaloids was synthesized from a densely functionalized cyclohexane derivative. An alkene and two cyanoformamide groups are used to form two new rings and a new quaternary stereocenter in a cascade reaction, which involves two Pd-catalyzed C-C bond activation steps. The synthesis of the cascade precursor involves an intramolecular Staudinger reaction of a vicinal diester that gives a [3.2.1]azabicyclooctane derivative, allowing the regioselective introduction of a monosubstituted alkene.

Original language	English (US)
Pages (from-to)	6149-6154
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.9b02331
State	Published - Aug 2 2019

Bibliographical note

Funding Information:
We thank the National Institutes of Health (R01 GM095559) for funding this work. We also thank Dr. Letitia Yao (UMN) for assistance with 2D NMR experiments and Prof. Daniel Everson (CSU Chico) for preliminary studies into the synthesis of 4 .

Publisher Copyright:
Copyright © 2019 American Chemical Society.

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abstract = "The diazatricyclic core of the madangamine alkaloids was synthesized from a densely functionalized cyclohexane derivative. An alkene and two cyanoformamide groups are used to form two new rings and a new quaternary stereocenter in a cascade reaction, which involves two Pd-catalyzed C-C bond activation steps. The synthesis of the cascade precursor involves an intramolecular Staudinger reaction of a vicinal diester that gives a [3.2.1]azabicyclooctane derivative, allowing the regioselective introduction of a monosubstituted alkene.",

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Synthesis of the Madangamine Alkaloid Core by a C-C Bond Activation Cascade

Abstract

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