Literature DB >> 24279324

Formal synthesis of (±)-cycloclavine.

Wei Wang1, Jia-Tian Lu, Hao-Li Zhang, Zi-Fa Shi, Jing Wen, Xiao-Ping Cao.   

Abstract

An efficient formal synthesis of (±)-cycloclavine is achieved in seven steps and 27% overall yield from the known 2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde. Key features include an iron(III)-catalyzed aza-Cope-Mannich cyclization and an intramolecular Heck reaction or a self-terminating 6-exo-trig aryl radical-alkene cyclization.

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Year:  2013        PMID: 24279324     DOI: 10.1021/jo4023588

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Eight-Step Enantioselective Total Synthesis of (-)-Cycloclavine.

Authors:  Stephanie R McCabe; Peter Wipf
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-18       Impact factor: 15.336

Review 2.  Total synthesis, biosynthesis and biological profiles of clavine alkaloids.

Authors:  Stephanie R McCabe; Peter Wipf
Journal:  Org Biomol Chem       Date:  2016-05-24       Impact factor: 3.876

3.  Discovery and Reconstitution of the Cycloclavine Biosynthetic Pathway-Enzymatic Formation of a Cyclopropyl Group.

Authors:  Dorota Jakubczyk; Lorenzo Caputi; Anaëlle Hatsch; Curt A F Nielsen; Melanie Diefenbacher; Jens Klein; Andrea Molt; Hartwig Schröder; Johnathan Z Cheng; Michael Naesby; Sarah E O'Connor
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-02-25
  3 in total

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