Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation |
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Authors: | Andrus Merritt B Hicken Erik J Stephens Jeffrey C Bedke D Karl |
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Institution: | Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, Utah 84602-5700, USA. mbandrus@chem.byu.edu |
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Abstract: | The total synthesis of the farnesyltransferase inhibitor kurasoin A has been achieved using a novel asymmetric phase-transfer-catalyzed glycolate alkylation reaction. 2,5-Dimethoxyacetophenone 7 with cinchonidinium catalyst 9(10 mol %) and hydroxide base with pivaloyl benzyl bromide 8 provided S-alkylation product 10 in high yield (80-99%) and excellent enantioselectivity. Baeyer-Villiger oxidation, Weinreb amide formation, and benzyl Grignard addition to the TES-ether 17 gave the protected target. Lithium hydroxide and peroxide generated kurasoin A (alpha](D) +8.4 degrees ) without isomerization. |
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