Total synthesis of cyclopiamide A and speradine E

Described is a total synthesis of the related alkaloids, cyclopiamide A and speradine E, via a unified strategy that also delivers the natural product aspergilline A. Key steps include metal-free conversion of a malonyl chloride and propargylamine to an intermediate pyrrolinone and a palladium catal...

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Bibliographic Details
Published in:Tetrahedron 2018-09, Vol.74 (38), p.5085-5088
Main Authors: Nakhla, Mina C., Weeks, Kendall N., Navarro Villalobos, Mauricio, Wood, John L.
Format: Article
Language:English
Subjects:
Aspergilline A speradine E
Cyclopiamide A
Indole alkaloids
Natural products
Total synthesis
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Summary:Described is a total synthesis of the related alkaloids, cyclopiamide A and speradine E, via a unified strategy that also delivers the natural product aspergilline A. Key steps include metal-free conversion of a malonyl chloride and propargylamine to an intermediate pyrrolinone and a palladium catalyzed decarboxylation/aromatization sequence that delivers the requisite tetracyclic core. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.02.039