Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.
The BC ring system of upenamide was assembled using a stereoselective Diels-Alder reaction followed by a Staudinger/aza-Wittig/imine hydrolysis reaction. Stereoselective aldol coupling with an aldehyde that incorporates the DE ring system led to an advanced synthetic intermediate en route to the marine alkaloid upenamide.
Luo
Zhushou
Z
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Peplowski
Katherine
K
Sulikowski
Gary A
GA
D018360:Crystallography, X-Ray; D006868:Hydrolysis; D008958:Models, Molecular; D008968:Molecular Conformation; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011807:Quinolizines; D013141:Spiro Compounds; C418125:upenamide