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Synlett 2009(4): 653-657  
DOI: 10.1055/s-0028-1087809
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Kurasoin B Using Phase-Transfer-Catalyzed Acylimidazole Alkylation

Michael A. Christiansen, Aaron W. Butler, Amanda R. Hill, Merritt B. Andrus*
Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, UT 84602, USA
Fax: +1(801)4220153; e-Mail: mbandrus@chem.byu.edu;
Further Information

Publication History

Received 25 August 2008
Publication Date:
16 February 2009 (online)

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Abstract

The hydroxy ketone natural product kurasoin B is synthesized using a phase-transfer-catalyzed alkylation reaction with benzyloxyacetyl imidazole. A biscinchonidinium dimethylnaphthalene catalyst allowed for high yield and near complete selectivity (99% ee) for the S-product using 3-methylbromoindole as the electrophile.

Key words

alkylations - asymmetric catalysis - asymmetric synthesis - natural products - total synthesis

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