Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues
AB Smith, JB Sperry, Q Han
Index: Smith III, Amos B.; Sperry, Jeffrey B.; Han, Qiang Journal of Organic Chemistry, 2007 , vol. 72, # 18 p. 6891 - 6900
Full Text: HTML
Citation Number: 42
Abstract
Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components,(-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first-and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein ...
Related Articles:
[Moon, Hyung Ryong; Choi, Won Jun; Kim, Hea Ok; Jeong, Lak Shin Tetrahedron Asymmetry, 2002 , vol. 13, # 11 p. 1189 - 1193]
Triply convergent synthesis of (-)-prostaglandin E2 methyl ester
[Johnson; Penning Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4726 - 4735]
Radical-mediated stannylation of vinyl sulfones: access to novel 4′-modified neplanocin A analogues
[Kumamoto, Hiroki; Deguchi, Kazuki; Wagata, Tadashi; Furuya, Yuu; Odanaka, Yuki; Kitade, Yukio; Tanaka, Hiromichi Tetrahedron, 2009 , vol. 65, # 38 p. 8007 - 8013]
Total synthesis of (±)-nardoaristolone B and its analogues
[Clive, Derrick L. J.; Liu, Dazhan Journal of Organic Chemistry, 2008 , vol. 73, # 8 p. 3078 - 3087]
[Journal of Organic Chemistry, , vol. 69, # 11 p. 3993 - 3996]