Biomimetic total synthesis of (+)-himbacine.
On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reductive work up. Compound 11 was converted into (+)-himbacine in four synthetic steps. [reaction: see text]
Tchabanenko
Kirill
K
Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, United Kingdom.
Adlington
Robert M
RM
Cowley
Andrew R
AR
Baldwin
Jack E
JE
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000447:Aldehydes; D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes; D005663:Furans / Q000138:chemical synthesis*; D008958:Models, Molecular; D009281:Naphthalenes / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid
D000447:Aldehydes; D000470:Alkaloids; D000475:Alkenes; D005663:Furans; D009281:Naphthalenes; D010880:Piperidines; C004511:butenolide; D014269:Trifluoroacetic Acid; C048172:himbacine; D015107:4-Butyrolactone