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A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.

ABSTRACT: [reaction: see text] A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

SUBMITTER: Bertrand MB 

PROVIDER: S-EPMC2613785 | biostudies-literature | 2006 May

REPOSITORIES: biostudies-literature

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A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.

Bertrand Myra Beaudoin MB   Wolfe John P JP  

Organic letters 20060501 11

[reaction: see text] A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups. ...[more]

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