Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid

作者：Hethcox J Caleb; Shanahan Charles S; Martin Stephen F^*

来源：Tetrahedron, 2015, 71(37): 6361-6368.

DOI：10.1016/j.tet.2015.05.023

• Total synthesis
• Conjugate addition
• Chiral auxiliary
• Cuprate
• Succinate

Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral gamma-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.

• 出版日期2015-9-16