Stereoselective one-step construction of vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton: total synthesis of (+/-)-maritidine

TitleStereoselective one-step construction of vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton: total synthesis of (+/-)-maritidine
Publication TypeJournal Article
Year of Publication2009
AuthorsPandey, G, Gupta, NR, Pimpalpalle, TM
JournalOrganic Letters
Volume11
Issue12
Pagination2547-2550
Date PublishedJUN
ISSN1523-7060
Abstract

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.
DOI10.1021/ol900806m
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)5.250
Divison category: 
Organic Chemistry