Stereoselective one-step construction of vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton: total synthesis of (+/-)-maritidine.
The challenging vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton are created in a single step utilizing intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The application of the chemistry is demonstrated by synthesizing (+/-)-maritidine.
Pandey
Ganesh
G
Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India. gp.pandey@ncl.res.in
Gupta
Nishant R
NR
Pimpalpalle
Tukaram M
TM
D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C544041:5,10b-ethanophenanthridine; D006576:Heterocyclic Compounds, 4 or More Rings; D010617:Phenanthridines; C476903:maritidine