Synfacts 2018; 14(03): 0221
DOI: 10.1055/s-0037-1609241
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Concise Synthesis of the Alkaloid (±)-Aspergilline A

Contributor(s):
Erick M. Carreira
,
Philipp Sondermann
Nakhla MC. Wood JL. * Baylor University, Waco, USA
Total Synthesis of (±)-Aspergilline A.

J. Am. Chem. Soc. 2017;
139: 18504-18507
Further Information

Publication History

Publication Date:
15 February 2018 (online)

 

Significance

Aspergilline A was isolated from the fungus Aspergillus versicolor and possesses activity against the tobacco mosaic virus as well as anti-cancer activity. The Wood group reports a synthesis relying on an elegant pyrrolinone formation and a formal [3+2] cycloaddition.


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Comment

Acylation followed by addition to an alkyne and double-bond isomerization transforms C into E. Mukaiyama aldol reaction creates the core structure in F. Imidate G undergoes formal cycloaddition with cyclopropenone to form I which is further transformed into the indole alkaloid aspergilline A through an oxidation–acetalization–decarboxylation sequence.


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