Octacidomycine, III: Synthetische Strukturanaloga aus C5-Bausteinen / Octacidomycins, III: Synthetic Structural Analogues from C5-Units

1995 ◽  
Vol 50 (10) ◽  
pp. 1550-1556
Author(s):  
Andreas Krause ◽  
Helmut Lackner
Keyword(s):  
Total Synthesis ◽  
Tetracarboxylic Acid ◽  
Unknown Type ◽  
Structural Analogues

The total synthesis of an isoprenoid-like analogue (2) of octacidomycin (1). a novel oligocarboxylic acid antibiotic, is described. Starting from 3 (Scheme 1) and the tetraethylester of 1,11-dibromoundecane-4,4,8,8,-tetracarboxylic acid (6) as a key compound systematical fragment condensations lead to the pentadeccicarboxylic acid 12 and hence to the 1,3,7,11,15,19,23,27-heptacosane-octacarboxylic acid 2. This contains regularly connected C5- instead of C7-units and shows contracted distances between the acid groups. The newly developed synthesis yields a hitherto unknown type of oligocarboxylic acids and some useful intermediates with one or two terminal vinylic functions (13-15 ).

scholarly journals The efficient synthesis of 1-deoxymannojirimycin and its derivatives

2021 ◽  
Author(s):  
◽  
Benjamin Mark Mandinka Deeble
Keyword(s):  
Total Synthesis ◽  
Lysosomal Storage Diseases ◽  
Heterocyclic Ring ◽  
Lysosomal Storage ◽  
Synthetic Strategy ◽  
Anti Cancer ◽  
Structural Analogues ◽  
Treatment Of Diabetes ◽  
Significant Effort ◽  
Selection Of

<p>Azasugars are structural analogues of carbohydrates whereby the oxygen in the heterocyclic ring is substituted for a nitrogen. These carbohydrates are an important class of compounds with medicinal bioactivities and have shown potential for the treatment of diabetes, viral-infection, cancers, and lysosomal storage diseases. 1-deoxymannojirimycin (DMJ), is a mannosidase inhibiting azasugar which has shown anti-cancer and anti-viral activity. There has been significant effort put towards developing methodology to produce this compound and libraries of its derivatives. This thesis presents the synthesis of DMJ and a selection of its derivatives via an efficient 4 step methodology from a carbohydrate starting material, exploiting chemo and regioselective reactions to allow for a total synthesis with minimal use of protecting groups. The synthesis of DMJ, using the methodology developed herein, surpasses published syntheses in efficiency. This synthetic strategy was then used for the preparation of N-functionalised DMJ derivatives without the requirement of additional synthetic steps. To illustrate the versatility of this methodology, a selection of derivatives incorporating different functionalities have been synthesised.</p>

Total Synthesis, Stereochemical Assignment, and Biological Activity of Chamuvarinin and Structural Analogues

2013 ◽  
Vol 19 (25) ◽  
pp. 8309-8320 ◽  
Author(s):  
Gordon J. Florence ◽  
Joanne C. Morris ◽  
Ross G. Murray ◽  
Raghava R. Vanga ◽  
Jonathan D. Osler ◽  
...  
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Stereochemical Assignment ◽  
Structural Analogues

Systemic Study on the Biogenic Pathways of Yezo’otogirins: Total Synthesis and Antitumor Activities of (±)-Yezo’otogirin C and Its Structural Analogues

2014 ◽  
Vol 80 (2) ◽  
pp. 836-846 ◽  
Author(s):  
Wei Yang ◽  
Jingming Cao ◽  
Mengxun Zhang ◽  
Rongfeng Lan ◽  
Lizhi Zhu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Antitumor Activities ◽  
Structural Analogues

scholarly journals Chemoenzymatic Total Synthesis of Sorbicatechol Structural Analogues and Evaluation of Their Antiviral Potential

ChemBioChem ◽  
2019 ◽  
Vol 21 (4) ◽  
pp. 492-495
Author(s):  
Anna Sib ◽  
Tobias M. Milzarek ◽  
Alexander Herrmann ◽  
Lila Oubraham ◽  
Jonas I. Müller ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Structural Analogues

Synthesis of the cyanobacterial metabolite nostodione A, structural studies and potent antiparasitic activity against Toxoplasma gondii

2015 ◽  
Vol 13 (39) ◽  
pp. 10015-10024 ◽  
Author(s):  
James McNulty ◽  
Kunal Keskar ◽  
Hilary A. Jenkins ◽  
Nick H. Werstiuk ◽  
Claudia Bordón ◽  
...  
Keyword(s):  
Toxoplasma Gondii ◽  
Total Synthesis ◽  
Natural Product ◽  
Structural Studies ◽  
Antiparasitic Activity ◽  
Structural Analogues

A total synthesis of the cyanobacterial natural product nostodione A is reported involving a convergent, diversity-oriented route, enabling the assembly of a mini-library of structural analogues.

scholarly journals Total Synthesis and Evaluation of Phostriecin and Key Structural Analogues

2010 ◽  
Vol 75 (22) ◽  
pp. 7505-7513 ◽  
Author(s):  
Christopher P. Burke ◽  
Mark R. Swingle ◽  
Richard E. Honkanen ◽  
Dale L. Boger
Keyword(s):  
Total Synthesis ◽  
Structural Analogues
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