THE ABSOLUTE CONFIGURATION OF SOME INDOLE ALKALOIDS1
THE ABSOLUTE CONFIGURATION OF SOME INDOLE ALKALOIDS1
复制标题
一些吲哚生物碱的绝对构型1
DOI：
10.1021/ja01546a077
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发表时间：
1958
期刊：
影响因子：
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通讯作者：
N. V. Bringi
中科院分区：
文献类型：
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作者：
E. Wenkert;N. V. Bringi
将阿曲马林2（I）用醇碱处理，然后用酸水溶液短暂加热，得到半缩醛IV，mp 226-228（对于C19 H24 O2 N2实测：C，72.65; H，7.85; N，8.95），其经Wolff-Kishner还原得到醇V，mp 200-201（对于CwH，GON 2实测：C，76.62; N，9.12; N，9.82）。后者的Oppenauer氧化得到酮Via，mp 225-227（对于C19 H240 N2实测：C，76.98; H，8.35），其可通过Wolff-Kishner还原转化为二氢-衣菜烷3（VIb），其相同的mp 189，mmp 188-189，[a] 0-94（吡啶）和红外光谱与真实样品。二氢辛可胺4 - 5在吡啶溶液中甲苯磺酰化生成季氯化物VII，mp 320-321。对后者进行甲苯磺酸银处理，得到季甲苯磺酸盐VII，与mp 313-315相同（dec.），MMP 315（dec.），[a]o-69.5（90%甲醇）和红外光谱与二氢紫堇烷-theol的甲苯磺酰化和二甲基甲酰胺缩合得到的化合物
An alcoholic alkali treatment of ajmalicine2 (I), followed by short heating with aqueous acid, led to the hemiacetal IV, mp 226-228 (Found for C19H2402N2: C, 72.65; H, 7.85; N, 8.95), which on Wolff-Kishner reduction yielded the alcohol V, mp 200-201 (Found for CwH, GON2: C, 76.62;, 9.12; N, 9.82). Oppenauer oxidation of the latter gave the ketone Via, mp 225-227 (found for Ci9H240N2: C, 76.98; H, 8.35), which could be converted by Wolff-Kishner reduction to dihydro-eorynantheane3 (VIb), identical in mp 189, mmp 188-189,[a] 0—94 (pyridine) and infrared spectrum with an authentic specimen.Tosylation of dihydrocinchonamine4 5in pyridine solution ledto thequaternary chloride VII, mp 320-321. Silver tosylate treatment of the latter yielded the quaternary tosylate VII, identical in mp 313-315 (dec.), mmp 315 (dec.),[a] o—69.5 (90% methanol) and infrared spectrum with the compound obtained from the tosylation and dimethylformamide refluxing of dihydrocorynan-theol. 6