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Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification.

ABSTRACT: A tandem Diels-Alder/Schmidt reaction provided an efficient route for the exploration of unnatural Stemona alkaloid analogues. Thus, a series of tricyclic scaffolds were efficiently prepared and then elaborated into seven sets of functionalized analogues. These derivatives incorporated appended heterocycles, such as indoles and quinolines, or other diversity-incorporating moieties such as carbamates and amines. Both the scaffold-generation sequence and the diversification steps could be manipulated to provide regio- and diastereochemically pure products.

SUBMITTER: Frankowski KJ

PROVIDER: S-EPMC2710395 | biostudies-literature | 2008 Sep-Oct

REPOSITORIES: biostudies-literature

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Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification.

Frankowski Kevin J KJ Neuenswander Benjamin B Aubé Jeffrey J

Journal of combinatorial chemistry 20080813 5

A tandem Diels-Alder/Schmidt reaction provided an efficient route for the exploration of unnatural Stemona alkaloid analogues. Thus, a series of tricyclic scaffolds were efficiently prepared and then elaborated into seven sets of functionalized analogues. These derivatives incorporated appended heterocycles, such as indoles and quinolines, or other diversity-incorporating moieties such as carbamates and amines. Both the scaffold-generation sequence and the diversification steps could be manipula ...[more]

PMID: 18698827

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