Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine

Niphakis, Micah J; Georg, Gunda I.

View/Open

Georg_2010.pdf (463.2Kb)

Issue Date

2010-09-03

Author

Niphakis, Micah J

Georg, Gunda I.

Publisher

American Chemical Society

Type

Article

Article Version

Scholarly/refereed, author accepted manuscript

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo101051w.

Metadata

Show full item record

Abstract

This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C–H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24–26% overall yields.

Citation

Niphakis, M. J., & Georg, G. I. (2010). Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine. The Journal of Organic Chemistry, 75(17), 6019–6022. http://doi.org/10.1021/jo101051w

The University of Kansas prohibits discrimination on the basis of race, color, ethnicity, religion, sex, national origin, age, ancestry, disability, status as a veteran, sexual orientation, marital status, parental status, gender identity, gender expression and genetic information in the University’s programs and activities. The following person has been designated to handle inquiries regarding the non-discrimination policies: Director of the Office of Institutional Opportunity and Access, IOA@ku.edu, 1246 W. Campus Road, Room 153A, Lawrence, KS, 66045, (785)864-6414, 711 TTY.