Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids

Although the indole N-phosphinoyl derivative 4 undergoes n-BuLi deprotonation/electrophile quench to afford C-7-substituted products, its deprotection requires harsh conditions. On the other hand, the N-amide 12, upon sequential or one-pot C-2 metalation, silylation, C-7 metalation, and electrophile...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 11; pp. 1899 - 1902
Main Authors Hartung, CG, Fecher, A, Chapell, B, Snieckus
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 29.05.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AMARYLLIDACEAE ALKALOIDS
ROUTE
METHODOLOGY
HIPPADINE
REAGENTS
REACTIVITY
NITROGEN
C-3
LITHIATION
CYCLIZATION
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Summary:Although the indole N-phosphinoyl derivative 4 undergoes n-BuLi deprotonation/electrophile quench to afford C-7-substituted products, its deprotection requires harsh conditions. On the other hand, the N-amide 12, upon sequential or one-pot C-2 metalation, silylation, C-7 metalation, and electrophile treatment, furnishes indoles 7 in good overall yields. In combination with the Suzuki-Mlyaura protocol, C-7 aryl (heteroaryl)-substituted indoles 14 and 16 are obtained, including hippadine and pratosine, members of the pyrrolophenanthridone alkaloid family.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0344772