Syntheses of optically active trifluoronorcoronamic acids.
Syntheses of optically active trifluoronorcoronamic acid 6 and its diastereomer 9 are described. Highly stereospecific and diastereoselective S(N)2 cyclization of gamma-cyanohydrins 3a and 3b gave cyclopropyl nitriles 4a and 4b. Hydrolysis of the cyano group and deprotection of the amino group of 4a provide trifluoronorcoronamic acid 6. Hofmann rearrangement of the amide which was generated by hydrolysis of the cyano group and oxidative cleavage of the aryl ring of 4b to provide trifluoro-allo-norcoronamic acid 9.
Katagiri
T
T
Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan. uneyamak@cc.okayama-u.ac.jp
Irie
M
M
Uneyama
K
K
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D001427:Bacterial Toxins / Q000737:chemistry; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis; D011549:Pseudomonas; D013237:Stereoisomerism
D000596:Amino Acids; D001427:Bacterial Toxins; D003521:Cyclopropanes; D007192:Indenes; D009570:Nitriles; C058487:coronatine