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Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

ABSTRACT: The total syntheses of aglafolin, rocagloic acid, and rocaglamide using Nazarov cyclization are described. Generation of the necessary oxyallyl cation intermediate was accomplished via peracid oxidation of an allenol ether to generate an unusual oxycarbenium ion species that undergoes cyclization. The synthesis is efficient, highly diastereoselective, and strategically distinct from previous syntheses of rocaglamide.

SUBMITTER: Malona JA

PROVIDER: S-EPMC2732401 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

Malona John A JA Cariou Kevin K Frontier Alison J AJ

Journal of the American Chemical Society 20090601 22

The total syntheses of aglafolin, rocagloic acid, and rocaglamide using Nazarov cyclization are described. Generation of the necessary oxyallyl cation intermediate was accomplished via peracid oxidation of an allenol ether to generate an unusual oxycarbenium ion species that undergoes cyclization. The synthesis is efficient, highly diastereoselective, and strategically distinct from previous syntheses of rocaglamide. ...[more]

PMID: 19445456

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