Literature DB >> 11483073

Total synthesis of the sesquiterpene (+/-)-illudin C via an intramolecular nitrile oxide cycloaddition.

R A Aungst1, C Chan, R L Funk.   

Abstract

[reaction: see text] A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide-olefin cycloaddition.

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Year:  2001        PMID： 11483073     DOI： 10.1021/ol016314o

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


  5 in total

1.  Transition structures of diastereoselective 1,3-dipolar cycloadditions of nitrile oxides to chiral homoallylic alcohols.

Authors:  Jennifer A R Luft; Kieche Meleson; K N Houk
Journal:  Org Lett       Date:  2007-01-25       Impact factor: 6.005

2.  Synthesis of 2,2-Disubstituted Pentalenes and Indenes by a Useful Modification to Nakamura's DMCP [3+2]-Cycloaddition Protocol.

Authors:  Todd A Wenderski; Vincent Denatale; Thomas R R Pettus
Journal:  Synlett       Date:  2009-10-01       Impact factor: 2.454

3.  Design and development of FGF-23 antagonists: Definition of the pharmacophore and initial structure-activity relationships probed by synthetic analogues.

Authors:  Ryan P Downs; Zhousheng Xiao; Munachi O Ikedionwu; Jacob W Cleveland; Ai Lin Chin; Abigail E Cafferty; L Darryl Quarles; Jesse D Carrick
Journal:  Bioorg Med Chem       Date:  2020-11-18       Impact factor: 3.641

4.  Synthesis of illudalic acid and analogous phosphatase inhibitors.

Authors:  Harvey F Fulo; Nicole J Rueb; Robert Gaston; Paratchata Batsomboon; Kh Tanvir Ahmed; Amy M Barrios; Gregory B Dudley
Journal:  Org Biomol Chem       Date:  2021-12-15       Impact factor: 3.876

5.  Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans.

Authors:  He-Ping Chen; Zhen-Zhu Zhao; Zheng-Hui Li; Ze-Jun Dong; Kun Wei; Xue Bai; Ling Zhang; Chun-Nan Wen; Tao Feng; Ji-Kai Liu
Journal:  ChemistryOpen       Date:  2016-01-13       Impact factor: 2.911
  5 in total

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