An intramolecular aza-[3+3] annulation approach to azaphenalene alkaloids. Total synthesis of myrrhine.
A detailed account on the stereoselective total syntheses of azaphenalene alkaloids via an intramolecular aza-[3+3] annulation strategy is described here. All five members of the Coccinellidae family of defensive alkaloids were prepared from the same common intermediate, which was derived from a stereoselective aza-[3+3] annulation reaction.
Gerasyuto
Aleksey I
AI
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Rennebohm Hall, 777 Highland Avenue, Madison, Wisconsin 53705, USA.
Hsung
Richard P
RP
D000470:Alkaloids / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002329:Carmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D011799:Quinazolines / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000470:Alkaloids; D001372:Aza Compounds; D007769:Lactams; D020005:Propanols; D011799:Quinazolines; C511678:hippodamine; C519421:myrrhine; D014867:Water; C006463:allyl alcohol; D002329:Carmine