Benzothiazines in synthesis. A total synthesis of pseudopteroxazole.
An enantioselective total synthesis of the naturally occurring antitubercular agent pseudopteroxazole is described. The synthesis is organized around the use of a stereoselective, intramolecular addition of a sulfoximine carbanion to an alpha,beta-unsaturated ester to form an enantiomerically pure benzothiazine. Other important processes include a completely stereoselective intramolecular Friedel-Crafts alkylation and a stereoselective and regioselective hydrogenation. [structure: see text]
Harmata
Michael
M
Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, USA. harmatam@missouri.edu
Hong
Xuechuan
X
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013843:Thiazines / Q000138:chemical synthesis*
D000995:Antitubercular Agents; D004224:Diterpenes; D010080:Oxazoles; D013843:Thiazines; C433836:pseudopteroxazole