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Synthesis of the pentacyclic skeleton of the indole alkaloid arboflorine.

ABSTRACT: An effective synthesis of the pentacyclic core of the unusual Kopsia alkaloid arboflorine is reported. The success of the synthetic route rested on the use of a borylative C-H functionalization reaction, a convergent Suzuki cross-coupling to a C(2) halogenated indole, and an unprecedented transannular dehydrogenative C-N bond forming reaction.

SUBMITTER: Leal RA

PROVIDER: S-EPMC3481541 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Synthesis of the pentacyclic skeleton of the indole alkaloid arboflorine.

Leal Raul A RA Beaudry Danial R DR Alzghari Saeed K SK Sarpong Richmond R

Organic letters 20120928 20

An effective synthesis of the pentacyclic core of the unusual Kopsia alkaloid arboflorine is reported. The success of the synthetic route rested on the use of a borylative C-H functionalization reaction, a convergent Suzuki cross-coupling to a C(2) halogenated indole, and an unprecedented transannular dehydrogenative C-N bond forming reaction. ...[more]

PMID: 23020147

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