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

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.

SUBMITTER: Niphakis MJ

PROVIDER: S-EPMC2948484 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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

Niphakis Micah J MJ Georg Gunda I GI

The Journal of organic chemistry 20100901 17

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. ...[more]

PMID: 20704319

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