Natural product synthesis via green chemical approach: Solid-to-solid photodecarbonylation

ORGN 88

Arunkumar Natarajan, anatara@chem.ucla.edu, Danny Chung Yin Ng, and Miguel Garcia-Garibay, mgg@chem.ucla.edu. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA 90095-1569
Despite the prevalence of natural products with adjacent chiral quarternary centers, their construction via general synthetic strategies remains a challenging task. We accomplish that in a simple and efficient manner via solid-to-solid photochemical decarbonylation of readily available hexa-substituted ketone precursors. One such example is a-cuparenone, a sesquiterpeneketone which is a secondary metabolite isolated in both enantiomers from different plant specimens. This paper describe the progress in the synthesise the (+) and (-) cuperanones using the chiral auxiliary strategy. Solid-to-solid reactions pave a environmentally benign approach to conduct solvent-free chemical reactions and overcome synthetic challenges for production of specialty chemicals.

 

Physical Organic Chemistry: Calculations, Mechanisms, Photochemistry, and High-Energy Species
1:00 PM-5:20 PM, Sunday, 10 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

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