Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid.
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 to date, but several attempts to prepare other succinate-derived natural products, such as pilocarpine and antrodin E, were unsuccessful.
Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
J Caleb
JC
Hethcox
Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
Charles S
CS
Shanahan
Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
Stephen F
SF
Martin
Chiral Auxiliary; Conjugate Addition; Cuprate; Succinate; Total Synthesis