111393-29-4Relevant articles and documents
Divergent Diels-Alder methodology from methyl coumalate toward functionalized aromatics
Lee, Jennifer J.,Kraus, George A.
supporting information, p. 2366 - 2368 (2013/06/26)
An inverse electron-demand Diels-Alder reaction between methyl coumalate and electron-rich dienophiles produces substituted benzoates. A high-yielding, single-pot procedure transforms readily accessible vinyl ether, ketal, or orthoester dienophiles into functionalized aromatic systems in a versatile route.
Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A.
Hashizume,Ito,Yamada,Nagashima,Kanao,Tomoda,Sunazuka,Kumagai,Omura
, p. 512 - 520 (2007/10/02)
To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxe tanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.