Synthesis of the Pentacyclic Skeleton of the Indole Alkaloid Arboflorine

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 transannul...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 20; pp. 5350 - 5353
Main Authors Leal, Raul A, Beaudry, Danial R, Alzghari, Saeed K, Sarpong, Richmond
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.10.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Science & Technology
Secologanin Tryptamine Alkaloids - chemical synthesis
AMINATION
LYCOPODIUM ALKALOIDS
REDUCTION
HECK
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Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302535r