Enantioselective synthesis for the (-)-antipode of the pyrazinone marine alkaloid, hamacanthin A.
A short enantioselective total synthesis for the (-)-antipode of the antifungal marine alkaloid, hamacanthin A, (6R)-3,6-bis(6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone, is described. This synthesis proceeds through the coupling of 3-indolyl-alpha-oxoacetyl chloride and 3-indolyl azidoethylamine, followed by intramolecular aza-Wittig type cyclization. A concise and useful approach for the synthesis of (1R)-1-(indol-3-yl)-2-azidoethylamine using the Sharpless asymmetric dihydroxylation reaction followed by stereospecific azidation is also presented.
Jiang
B
B
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, Peoples' Republic of China. jiangb@pub.sioc.ac.cn
Yang
C G
CG
Wang
J
J
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D011161:Porifera / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000935:Antifungal Agents; D026121:Indole Alkaloids; D007211:Indoles; D011719:Pyrazines; C091307:hamacanthine A