Chiral 2-bromo-4-hydroxy-cyclohexa-2,5-dienone derivatives: A versatile chiron for natural product synthesis

ORGN 306

Todd Wenderski, twenderski@chem.ucsb.edu, Christophe Hoarau, Kristopher Gowin, Ryan Van De Water, Lupe H. Mejorado, mejorado@chem.ucsb.edu, and Thomas R. R. Pettus, pettus@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106
Diasteroselective oxidative dearomatization of 2-bromo-4-alkyl resorcinols gives useful cyclohexadienone building blocks for natural products. The unusual and versatile reactions of the 2-bromo-4-hydroxy-4-methylcylcohexa-2,5-dienone product will be presented. A formal synthesis of (-)-kessane is represented by (S)-4-hydroxy-4-methylcyclohex-2-enone.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Monday, 11 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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