Total Synthesis of Aristolactams via a One-Pot Suzuki−Miyaura Coupling/Aldol Condensation Cascade Reaction

A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki−Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 16; pp. 3543 - 3546
Main Authors Kim, Joa Kyum, Kim, Young Ha, Nam, Ho Tae, Kim, Bum Tae, Heo, Jung-Nyoung
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2008
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Boronic Acids - chemical synthesis
Boronic Acids - chemistry
Chemistry
Chemistry, Organic
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Isoindoles - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Phenanthrenes - chemical synthesis
Phenanthrenes - chemistry
Physical Sciences
Plant Extracts - chemical synthesis
Plant Extracts - chemistry
Science & Technology
Stereoisomerism
ORGANIC-SYNTHESIS
FISSISTIGMA-OLDHAMII
DIOXOAPORPHINES
4,5-DIOXOAPORPHINES
CEPHARANONE
PIPEROLACTAM-C
ARISTOLOCHIC ACIDS
ARISTOLOLACTAMS
ALKALOIDS
CONSTITUENTS
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Summary:A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki−Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol801291k