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Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (−)-dihydroprotolichesterinic acid
- Hethcox, J. Caleb, Shanahan, Charles S., Martin, Stephen F.
- Tetrahedron 2015 v.71 pp. 6361-6368
- chemical reactions, chemical structure, fumarates, pilocarpine
- 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.