Enantioselective total synthesis of (-)-deoxoapodine
Author(s)Kang, Taek; White, Kolby L.; Mann, Tyler J.; Hoveyda, Amir H.; Movassaghi, Mohammad
MetadataShow full item record
The first enantioselective total synthesis of (−)-deoxoapodine is described. Our synthesis of this hexacyclic aspidosperma alkaloid includes an efficient molybdenum-catalyzed enantioselective ring-closing metathesis reaction for the desymmetrization of an advanced intermediate that introduces the C5-quaternary stereocenter. After C21-oxygenation, the pentacyclic core was accessed by electrophilic C19-amide activation and transannular spirocyclization. A biogenetically inspired dehydrative C6-etherification reaction proved highly effective to secure the F-ring and the fourth contiguous stereocenter of (−)-deoxoapodine with complete stereochemical control.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Angewandte Chemie International Edition
Kang, Taek, et al., "Enantioselective total synthesis of (-)-deoxoapodine." Angewandte Chemie International Edition 56, 44 (Sept. 2017): p. 13857-60 doi 10.1002/anie.201708088 ©2017 Author(s)
Author's final manuscript