851960-34-4Relevant academic research and scientific papers
Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid
Hethcox, J. Caleb,Shanahan, Charles S.,Martin, Stephen F.
, p. 6361 - 6368 (2015/08/18)
Abstract Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral γ-alkoxycrotonates and fumarates are disclosed. This methodology was applied to the shortest total synthesis of (-)-dihydroprotolichesterinic acid
Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to a chiral fumarate
Hethcox, J. Caleb,Shanahan, Charles S.,Martin, Stephen F.
, p. 2074 - 2076 (2013/04/23)
A diastereoselective conjugate addition of a variety of monoorganocuprates, Li[RCuI], to chiral fumarates to provide funtionalized succinates has been developed. The utility of this reaction is demonstrated in a concise total synthesis of (-)-dihydroprotolichesterenic acid that required only four steps and proceeded in an overall 31% yield.
