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Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C.

ABSTRACT: Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, followed by excision of the carbamate, yields (+/-)-2-epi-pumiliotoxin C.

SUBMITTER: Fearnley SP

PROVIDER: S-EPMC2872181 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C.

Fearnley Stephen Philip SP Thongsornkleeb Charnsak C

The Journal of organic chemistry 20100201 3

Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, followed by excision of the carbamate, yields (+/-)-2-epi-pumiliotoxin C. ...[more]

PMID: 20039614

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