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Concise, stereocontrolled synthesis of the citrinadin B core architecture.

ABSTRACT: A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6-disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

SUBMITTER: Guerrero CA

PROVIDER: S-EPMC3217263 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Concise, stereocontrolled synthesis of the citrinadin B core architecture.

Guerrero Carlos A CA Sorensen Erik J EJ

Organic letters 20110906 19

A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6-disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core. ...[more]

PMID: 21894952

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