Diversification of Monoterpene Indole Alkaloid Analogs through Cross-Coupling

Catharanthus roseus monoterpene indole alkaloid analogs have been produced via a combination of biosynthetic and chemical strategies. Specifically, introduction of a chemical handlea chlorine or a bromineinto the target molecule by mutasynthesis, followed by postbiosynthetic chemical derivatizatio...

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Bibliographic Details
Published in:Organic letters 2013-06, Vol.15 (11), p.2850-2853
Main Authors: Runguphan, Weerawat, O’Connor, Sarah E
Format: Article
Language:English
Subjects:
Bromine - chemistry
Catalysis
Chlorine - chemistry
Cross-Linking Reagents - chemistry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Indole Alkaloids - metabolism
Molecular Structure
Monoterpenes - chemical synthesis
Monoterpenes - chemistry
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Summary:Catharanthus roseus monoterpene indole alkaloid analogs have been produced via a combination of biosynthetic and chemical strategies. Specifically, introduction of a chemical handlea chlorine or a bromineinto the target molecule by mutasynthesis, followed by postbiosynthetic chemical derivatization using Pd-catalyzed Suzuki-Miyaura cross-coupling reactions robustly afforded aryl and heteroaryl analogs of these alkaloids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401179k