Literature DB >> 16901172

Total synthesis of antofine using the net [5+5]-cycloaddition of gamma,delta-unsaturated carbene complexes and 2-alkynylphenyl ketones as a key step.

Alejandro Camacho-Davila1, James W Herndon.   

Abstract

A compound containing all of the carbons of the anticancer agent antofine was produced in a single step from the coupling of a gamma,delta-unsaturated carbene complex with a 2-alkynylphenyl ketone derivative. Subsequent conversion to antofine was effected in three steps.

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Year:  2006        PMID： 16901172     DOI： 10.1021/jo061053n

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


  9 in total

1.  Total synthesis of (+)-antofine and (-)-cryptopleurine.

Authors:  Weijiang Ying; James W Herndon
Journal:  European J Org Chem       Date:  2013-05-01

2.  The [5+5] route to the phenanthrene skeleton.

Authors:  James W Herndon; Bishnu Dhakal
Journal:  ARKIVOC       Date:  2016-06-21       Impact factor: 1.140

3.  Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

Authors:  Charles S Shanahan; Phong Truong; Savannah M Mason; John S Leszczynski; Michael P Doyle
Journal:  Org Lett       Date:  2013-07-05       Impact factor: 6.005

4.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

5.  Electronic Control of Product Distribution in the [5+5]-Coupling of ortho-Alkynylbenzaldehyde Derivatives and γ,δ-Unsaturated Carbene Complexes.

Authors:  Alejandro Camacho-Davila; Lalith S R Gamage; Zhipeng Wang; James W Herndon
Journal:  Tetrahedron       Date:  2010-07       Impact factor: 2.457

6.  Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.

Authors:  Sherry R Chemler
Journal:  Curr Bioact Compd       Date:  2009-03-01

7.  Total synthesis of phenanthroindolizidine alkaloids (+/-)-antofine, (+/-)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity.

Authors:  Chung-Ren Su; Amooru G Damu; Po-Cheng Chiang; Kenneth F Bastow; Susan L Morris-Natschke; Kuo-Hsiung Lee; Tian-Shung Wu
Journal:  Bioorg Med Chem       Date:  2008-04-18       Impact factor: 3.641

8.  Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives.

Authors:  Shaofeng Duan; Karen Cress; Kris Waynant; Elias Ramos-Miranda; James W Herndon
Journal:  Tetrahedron       Date:  2007-04-02       Impact factor: 2.457

9.  One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes.

Authors:  Priyabrata Roy; Binay Krishna Ghorai
Journal:  Beilstein J Org Chem       Date:  2010-05-25       Impact factor: 2.883
  9 in total

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