Literature DB >> 11671566

Synthesis of Angucyclines. 8. Biomimetic-Type Synthesis of Rabelomycin, Tetrangomycin, and Related Ring B Aromatic Angucyclinones.

Karsten Krohn1, Norbert Böker, Ulrich Flörke, Christian Freund.   

Abstract

The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared in a biomimetic-type synthesis by two successive aldol cyclizations starting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions. The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the phenolic anthraquinones 16a-c upon treatment with excess NMO.

Entities:  

Year:  1997        PMID： 11671566     DOI： 10.1021/jo9622587

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


  4 in total

1.  Enzymatic total synthesis of rabelomycin, an angucycline group antibiotic.

Authors:  Madan Kumar Kharel; Pallab Pahari; Hui Lian; Jürgen Rohr
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Identification of the function of gene lndM2 encoding a bifunctional oxygenase-reductase involved in the biosynthesis of the antitumor antibiotic landomycin E by Streptomyces globisporus 1912 supports the originally assigned structure for landomycinone.

Authors:  Lili Zhu; Bohdan Ostash; Uwe Rix; Mohammad Nur-E-Alam; Almuth Mayers; Andriy Luzhetskyy; Carmen Mendez; Jose A Salas; Andreas Bechthold; Victor Fedorenko; Jürgen Rohr
Journal:  J Org Chem       Date:  2005-01-21       Impact factor: 4.354

3.  11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a Streptomyces cyanogenus K62 mutant strain.

Authors:  Khaled A Shaaban; Chris Stamatkin; Chendil Damodaran; Jürgen Rohr
Journal:  J Antibiot (Tokyo)       Date:  2010-10-27       Impact factor: 2.649

4.  (-)-Shikimic Acid as a Chiral Building Block for the Synthesis of New Cytotoxic 6-Aza-Analogues of Angucyclinones.

Authors:  Natalia Quiñones; Santiago Hernández; Luis Espinoza Catalán; Joan Villena; Ivan Brito; Alan R Cabrera; Cristian O Salas; Mauricio A Cuellar
Journal:  Molecules       Date:  2018-06-12       Impact factor: 4.411
  4 in total

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