Synthesis of cis-3-hydroxy-2,6-disubstituted-piperidine alkaloids via an aza-Achmatowicz oxidation of N-tosylaminofurans

ORGN 925

Carolyn A. Leverett, Calever@emory.edu1, Albert Padwa, chemap@emory.edu1, and Michael P. Cassidy2. (1) Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, (2) Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037
Functionalized piperidines of the Cassia and Prosopis species have captured the attention of the organic community as both a synthetically challenging and biologically interesting group of alkaloids. As an approach to this class of alkaloids, we have utilized the aza-Achmatowicz oxidation of N-tosylaminofurans in order to prepare the piperidine alkaloids (±)-Azimic acid and (±)-Deoxocassine. This method provides easy access to the required cis-2-methyl-6-substituted piperidin-3-ol core. To further demonstrate the utility of the method, the total synthesis of (±)-Spicigerine and (±)-Cassine has been completed and a method for obtaining such alkaloids enantioselectively has also been developed. Following generation of the piperidine framework, the carboxylic acid side chain was converted to a versatile Weinreb amide intermediate that allowed for the introduction of a wide variety of substituent groups, thereby enabling access to a number of natural products.

 

Heterocycles and Aromatics
1:00 PM-4:40 PM, Thursday, 14 September 2006 Moscone Center -- Room 135, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006