The bromopentadienyl acrylate approach to himbacine.
[reaction: see text] The syntheses of 4,4a-didehydrohimbacine and 4,4a-didehydrohimandravine are presented. Key steps include an intramolecular Diels-Alder reaction of a bromopentadienyl acrylate and Suzuki-Miyaura and Stille coupling reactions.
Wong
Leon S-M
LS
School of Chemistry, University of Sydney, Sydney NSW 2006, Australia.
Sharp
Lisa A
LA
Xavier
Natacha M C
NM
Turner
Peter
P
Sherburn
Michael S
MS
D000179:Acrylates / Q000138:chemical synthesis*; D000470:Alkaloids / Q000138:chemical synthesis*; D005663:Furans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009281:Naphthalenes; D010276:Parasympatholytics / Q000737:chemistry*; D010880:Piperidines; D010946:Plants, Medicinal / Q000737:chemistry
D000179:Acrylates; D000470:Alkaloids; D005663:Furans; D007202:Indicators and Reagents; D009281:Naphthalenes; D010276:Parasympatholytics; D010880:Piperidines; C458302:bromopentadienyl acrylate; C048172:himbacine