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Literature DB >> 35225624

Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation.

Abstract

We describe a formal synthesis of 10-aza-9-oxakalkitoxin, the hydroxalog of the cytotoxic marine natural product kalkitoxin, that features Mukaiyama Markovnikov silyl peroxidation of a terminal alkene and N-O bond formation as the central enabling steps.

Entities: Chemical

Year: 2022 PMID： 35225624 PMCID： PMC9004444 DOI： 10.1021/acs.orglett.2c00349

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

16 in total

1. Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines.

Authors: Sandeep Dhanju; David Crich
Journal: Org Lett Date: 2016-04-07 Impact factor: 6.005

2. Synthesis, Cytotoxicity, and Genotoxicity of 10-Aza-9-oxakalkitoxin, an N,N,O-Trisubstituted Hydroxylamine Analog, or Hydroxalog, of a Marine Natural Product.

Authors: Sandeep Dhanju; Kapil Upadhyaya; Christopher A Rice; Scott D Pegan; Joseph Media; Frederick A Valeriote; David Crich
Journal: J Am Chem Soc Date: 2020-05-07 Impact factor: 15.419

3. Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides.

Authors: Lin Hu; Xiaojie Lu; Li Deng
Journal: J Am Chem Soc Date: 2015-06-29 Impact factor: 15.419

4. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test.

Authors: B N Ames; J Mccann; E Yamasaki
Journal: Mutat Res Date: 1975-12 Impact factor: 2.433

5. Stereoselective oxy-functionalization of gamma-silyl allylic alcohols with ozone: a facile synthesis of silyl peroxide and its reactions.

Authors: Masanori Murakami; Kyohei Sakita; Kazunobu Igawa; Katsuhiko Tomooka
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

6. Antillatoxin and kalkitoxin, ichthyotoxins from the tropical cyanobacterium Lyngbya majuscula, induce distinct temporal patterns of NMDA receptor-mediated neurotoxicity.

Authors: F W Berman; W H Gerwick; T F Murray
Journal: Toxicon Date: 1999-11 Impact factor: 3.033

7. Synthesis of Trialkylhydroxylamines by Stepwise Reduction of O-Acyl N,N-Disubstituted Hydroxylamines: Substituent Effects on the Reduction of O-(1-Acyloxyalkyl)hydroxylamines and on the Conformational Dynamics of N-Alkoxypiperidines.

Authors: Sandeep Dhanju; Brendan W Blazejewski; David Crich
Journal: J Org Chem Date: 2017-05-08 Impact factor: 4.354

Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation.

1. Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines.

2. Synthesis, Cytotoxicity, and Genotoxicity of 10-Aza-9-oxakalkitoxin, an N,N,O-Trisubstituted Hydroxylamine Analog, or Hydroxalog, of a Marine Natural Product.

3. Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides.

4. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test.

5. Stereoselective oxy-functionalization of gamma-silyl allylic alcohols with ozone: a facile synthesis of silyl peroxide and its reactions.

6. Antillatoxin and kalkitoxin, ichthyotoxins from the tropical cyanobacterium Lyngbya majuscula, induce distinct temporal patterns of NMDA receptor-mediated neurotoxicity.

7. Synthesis of Trialkylhydroxylamines by Stepwise Reduction of O-Acyl N,N-Disubstituted Hydroxylamines: Substituent Effects on the Reduction of O-(1-Acyloxyalkyl)hydroxylamines and on the Conformational Dynamics of N-Alkoxypiperidines.

8. Programmable Synthesis of 2-Deoxyglycosides.

9. Synthesis of O-tert-Butyl-N,N-disubstituted Hydroxylamines by N-O Bond Formation.

10. Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals.

1. The N,N,O-Trisubstituted Hydroxylamine Isostere and Its Influence on Lipophilicity and Related Parameters.