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Synthetic Studies on Dermacozines: First Synthesis of Dermacozines A, B and C
Author(s) -
Ghanta Venkata Rao,
Pasula Aparna,
Soma Laxminarayana,
Raman Balamurali
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600415
Subject(s) - regioselectivity , nitrile , chemistry , nitrogen atom , carbon atom , carbon fibers , catalysis , organic chemistry , group (periodic table) , combinatorial chemistry , medicinal chemistry , stereochemistry , ring (chemistry) , materials science , composite number , composite material
We herein, report the first total synthesis of Dermacozine A and B in moderate to high yields from a commercially available methyl 2‐bromo (or chloro)‐3‐nitrobenzoate in an atom efficient route. The key carbon–nitrogen and carbon‐carbon bond forming reactions involve inter and intra ‐molecular Pd (0) catalyzed N ‐arylations and regioselective Friedel‐Crafts benzoylation respectively. Nitrile group was used as a masked carboxylic group to differentially functionalize two carboxylic acids to achieve Dermacozine C.