Intramolecular formal aza-[3 + 3] cycloaddition approach to indoloquinolizidine alkaloids. A stereoselective total synthesis of (+/-)-tangutorine.
[reaction: see text] A 19-step stereoselective total synthesis of (+/-)-tangutorine is described here. The total synthesis features an intramolecular aza-[3 + 3] formal cycloaddition strategy and also a Heck coupling for constructing the C2-C3 bond. This work provides a novel approach toward the indoloquinolizidine family of alkaloids.
Luo
Shengjun
S
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Zificsak
Craig A
CA
Hsung
Richard P
RP
D000470:Alkaloids / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry*; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D001372:Aza Compounds; D002243:Carbolines; D045563:Indolequinones; D011807:Quinolizines; C485396:tangutorine