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

Niphakis, Micah James; Georg, Gunda I.

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Issue Date

2010-09-03

Author

Niphakis, Micah James

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.

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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

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