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J Org Chem. 2013 Sep 6;78(17):8645-54. doi: 10.1021/jo401262v. Epub 2013 Aug 27.

Emulating the logic of monoterpenoid alkaloid biogenesis to access a skeletally diverse chemical library.

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  • 1Department of Chemistry, University of Chicago, Chicago, Illinois 60607, USA.

Abstract

We have developed a synthetic strategy that mimics the diversity-generating power of monoterpenoid indole alkaloid biosynthesis. Our general approach goes beyond diversification of a single natural product-like substructure and enables production of a highly diverse collection of small molecules. The reaction sequence begins with rapid and highly modular assembly of the tetracyclic indoloquinolizidine core, which can be chemoselectively processed into several additional skeletally diverse structural frameworks. The general utility of this approach was demonstrated by parallel synthesis of two representative chemical libraries containing 847 compounds with favorable physicochemical properties to enable its subsequent broad pharmacological evaluation.

PMID:
23937288
PMCID:
PMC3842850
DOI:
10.1021/jo401262v
[PubMed - indexed for MEDLINE]
Free PMC Article
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