A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans

A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P­( t Bu)3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range o...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 18; pp. 4750 - 4753
Main Authors Chuang, Kangway V, Kieffer, Madeleine E, Reisman, Sarah E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Dipeptides - chemical synthesis
Dipeptides - chemistry
Indoles - chemistry
Molecular Conformation
Physical Sciences
Science & Technology
Stereoisomerism
Tryptophan - chemical synthesis
Tryptophan - chemistry
CROSS-COUPLINGS
ANALOGS
HECK REACTIONS
EFFICIENT ASYMMETRIC-SYNTHESIS
INTERNAL ALKYNES
HETEROANNULATION
CATALYST
2,3-DISUBSTITUTED INDOLES
ARYL CHLORIDES
ARYLBORONIC ACIDS
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Summary:A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P­( t Bu)3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent total synthesis of the bisindole natural product (−)-aspergilazine A.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02477