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. 2006 May 25;8(11):2353-6.
doi: 10.1021/ol0606435.

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

Myra Beaudoin Bertrand  1 , John P Wolfe
Affiliations

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

Myra Beaudoin Bertrand et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Key Disconnection and Stereocontrol
Scheme 2
Scheme 2
Synthesis of (±)-Preussin
Scheme 3
Scheme 3
Synthesis of (±)-3-epi-Preussin.
Scheme 4
Scheme 4
Synthesis of (+)-Preussin
See this image and copyright information in PMC

References

    1. Schwartz RE, Liesch J, Hensens O, Zitano L, Honeycutt S, Garrity G, Fromtling RA, Onishi J, Monaghan R. J. Antibiot. 1988;41:1774. - PubMed
    1. Johnson JH, Phillipson DW, Kahle AD. J. Antibiot. 1989;42:1184. - PubMed
    2. Kasahara K, Yoshida M, Eishima J, Takesako K, Beppu T, Horinouchi S. J. Antibiot. 1997;50:267. - PubMed
    1. Achenbach TV, Slater PE, Brummerhop H, Bach T, Müller R. Antimicrob. Agents Chemother. 2000;44:2794. - PMC - PubMed
    1. Kinzy TG, Harger JW, Carr-Schmid A, Kwon J, Shastry M, Justice M, Dinman JD. Virology. 2002;300:60. - PubMed
    1. Okue M, Watanabe H, Kasahara K, Yoshida M, Horinouchi S, Kitahara T. Biosci. Biotechnol. Biochem. 2002;66:1093. - PubMed

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