Literature DB >> 23586838

Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach.

Zhe Zhang1, Geoffrey M Giampa, Cristian Draghici, Qiufeng Huang, Matthias Brewer.   

Abstract

A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.

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Year:  2013        PMID： 23586838      PMCID： PMC3671602          DOI： 10.1021/ol4004993

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


  6 in total

1.  Differential inhibition of the serum cholinesterase phenotypes by solanine and solanidine.

Authors:  H HARRIS; M WHITTAKER
Journal:  Ann Hum Genet       Date:  1962-07       Impact factor: 1.670

2.  Lewis acid promoted carbon-carbon bond cleavage of gamma-silyloxy-beta-hydroxy-alpha-diazoesters.

Authors:  Cristian Draghici; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419

3.  Rapid and efficient preparation of free amino acids from strong acid salts on columns of crosslinked poly-4-vinylpyridine.

Authors:  D M Jewett; R L Ehrenkaufer
Journal:  Anal Biochem       Date:  1982-05-15       Impact factor: 3.365

4.  Preparation of tethered aldehyde ynoates and ynones by ring fragmentation of cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls.

Authors:  Ali Bayir; Cristian Draghici; Matthias Brewer
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

5.  Dual specificity of sterol-mediated glycoalkaloid induced membrane disruption.

Authors:  E A Keukens; T de Vrije; C H Fabrie; R A Demel; W M Jongen; B de Kruijff
Journal:  Biochim Biophys Acta       Date:  1992-10-05

6.  An efficient synthetic approach to polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones.

Authors:  Cristian Draghici; Qiufeng Huang; Matthias Brewer
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354
  6 in total
  3 in total

1.  Formal and total synthesis of (±)-cycloclavine.

Authors:  Nitinkumar D Jabre; Teruki Watanabe; Matthias Brewer
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

2.  A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.

Authors:  Geoffrey M Giampa; Jian Fang; Matthias Brewer
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005

3.  Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells.

Authors:  Svetlana K Vorontsova; Anton V Yadykov; Alexander M Scherbakov; Mikhail E Minyaev; Igor V Zavarzin; Ekaterina I Mikhaevich; Yulia A Volkova; Valerii Z Shirinian
Journal:  Molecules       Date:  2020-07-31       Impact factor: 4.411
  3 in total

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