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Total Synthesis of (±)-Gelsemine |
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| Authors: | Andrew Madin Christopher J O'Donnell Taeboem Oh David W Old Larry E Overman Matthew J Sharp |
| Abstract: | A complex molecular reorganization ( 1 → 2 ), a sequential anionic aza-Cope rearrangement and Mannich cyclization, and an unprecedented intramolecular Heck reaction of the tetrasubstituted double bond of a vinylogous carbamate are key steps in a new total synthesis of (±)-gelsemine ( 3 ). MOM=methoxymethyl, DBU=1,8-diazabicyclo5.4.0]undec-7-ene. |
| Keywords: | Alkaloids Palladium Pericyclic reactions Rearrangements Total synthesis |