Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine

Micah J. Niphakis; Gunda I. Georg

doi:10.1021/jo101051w

Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine

Micah J. Niphakis, Gunda I. Georg

Medicinal Chemistry

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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.

Original language	English (US)
Pages (from-to)	6019-6022
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	17
DOIs	https://doi.org/10.1021/jo101051w
State	Published - Sep 3 2010

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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.",

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Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine

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