Michel P, Rassat A, Daly J W, Spande T F
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0820, USA.
J Org Chem. 2000 Dec 29;65(26):8908-18. doi: 10.1021/jo000666b.
An efficient, high-yield stereospecific route to three (+/-)-5, 8-disubstituted indolizidines, (209B (I), 209I (II), 223J (III)) and two (+/-)-1,4-disubstituted quinolizidines (207I (IV), 233A (V)), racemates of alkaloids found in the skins of neotropical and Madagascan poison frogs is reported. The structures of the natural alkaloids were thereby established by chiral GC comparison with the exception of indolizidine 209B (I) for which a natural 209B could no longer be detected.
报道了一种高效、高产率的立体定向合成路线，用于合成三种（±）-5,8-二取代中氮茚（209B（I）、209I（II）、223J（III））和两种（±）-1,4-二取代喹嗪（207I（IV）、233A（V）），它们是在新热带和马达加斯加毒蛙皮肤中发现的生物碱的外消旋体。通过手性气相色谱比较确定了天然生物碱的结构，但中氮茚209B（I）除外，因为已无法检测到天然的209B。
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