A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.
A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
Kirill
K
Tchabanenko
Nigel S
NS
Simpkins
Louise
L
Male
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*
D000470:Alkaloids; C063230:gelsemine; D002244:Carbon; D010100:Oxygen