Journal
ORGANIC LETTERS
Volume 15, Issue 3, Pages 706-709Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400046n
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Funding
- NIGMS [GM-43214, GM-59316, GM-69721]
- Boehringer Ingelheim
- Eli Lilly
- National Science Foundation/Department of Energy [NSF/CHE 0822838]
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-AC02-06CH11357]
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A catalytic, enantioselective synthesis of (+)-reserpine Is reported. The route features a highly diastereoselective, chiral catalyst-controlled formal aza-Diels-Alder reaction between a 6-methoxytryptamine-derived dihydro-beta-carboline and an enantioenriched alpha-substituted enone to form a key tetracyclic intermediate. This approach addresses the challenge of setting the C3 stereogenic center by using catalyst control. Elaboration of the tetracycle to (+)-reserpine includes an intramolecular aldol cyclization and a highly diastereoselective hydrogenation of a sterically hindered enoate.
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