Literature DB >> 35058668

Synthesis and biological evaluation of 10-benzyloxy-Narciclasine.

Vincenzo Ticli1, Zhenze Zhao2, Liqin Du2, Alexander Kornienko2, Tomas Hudlicky1.   

Abstract

A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene dioxygenase-mediated hydroxylation, nitroso Diels-Alder reaction and intramolecular Heck cyclization. The unnatural derivative of narciclasine was subjected to biological evaluation and its activity was compared to other C-10 and C-7 compounds prepared previously.

Entities:  

Keywords:  Chemoenzymatic; Enantioselective synthesis; Narciclasine; Natural products; Synthesis

Year:  2021        PMID： 35058668      PMCID： PMC8765737          DOI： 10.1016/j.tet.2021.132505

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  17 in total

1.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.

Authors:  Sergey Vshyvenko; Jon Scattolon; Tomas Hudlicky; Anntherese E Romero; Alexander Kornienko
Journal:  Bioorg Med Chem Lett       Date:  2011-06-22       Impact factor: 2.823

3.  Total synthesis of bulbophylol-B.

Authors:  Jinshun Lin; Weige Zhang; Nan Jiang; Zeyu Niu; Kai Bao; Liang Zhang; Dailin Liu; Chao Pan; Xinsheng Yao
Journal:  J Nat Prod       Date:  2008-10-29       Impact factor: 4.050

Review 4.  Chemistry, biology, and medicinal potential of narciclasine and its congeners.

Authors:  Alexander Kornienko; Antonio Evidente
Journal:  Chem Rev       Date:  2008-05-20       Impact factor: 60.622

5.  Oxidative degradation of aromatic hydrocarbons by microorganisms. I. Enzymatic formation of catechol from benzene.

Authors:  D T Gibson; J R Koch; R E Kallio
Journal:  Biochemistry       Date:  1968-07       Impact factor: 3.162

6.  Narciclasine: an antimitotic substance from Narcissus bulbs.

Authors:  G Ceriotti
Journal:  Nature       Date:  1967-02-11       Impact factor: 49.962

7.  Toluene degradation by Pseudomonas putida F1. Nucleotide sequence of the todC1C2BADE genes and their expression in Escherichia coli.

Authors:  G J Zylstra; D T Gibson
Journal:  J Biol Chem       Date:  1989-09-05       Impact factor: 5.157

8.  Microbial oxidation of aromatics in enantiocontrolled synthesis. 2. Rational design of aza sugars (endo-nitrogenous). Total synthesis of +-kifunensine, mannojirimycin, and other glycosidase inhibitors.

Authors:  T Hudlicky; J Rouden; H Luna; S Allen
Journal:  J Am Chem Soc       Date:  1994-06       Impact factor: 15.419

9.  Isolation, structure, and synthesis of combretastatins A-1 and B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum.

Authors:  G R Pettit; S B Singh; M L Niven; E Hamel; J M Schmidt
Journal:  J Nat Prod       Date:  1987 Jan-Feb       Impact factor: 4.050

10.  Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination.

Authors:  Mark Lautens; Yuan-Qing Fang
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005
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  2 in total

1.  Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity.

Authors:  Lihi Habaz; Korey Bedard; Mitchell Smith; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Molecules       Date:  2022-06-14       Impact factor: 4.927

2.  Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine.

Authors:  Juana Goulart Stollmaier; Jared Thomson; Mary Ann Endoma-Arias; Razvan Simionescu; Alexandra Vernaza; Nakya Mesa-Diaz; Mitchell Smith; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Molecules       Date:  2022-06-28       Impact factor: 4.927
  2 in total

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