General and efficient strategy for erythrinan and homoerythrinan alkaloids:: Syntheses of (±)-3-demethoxyerythratidinone and (±)-erysotramidine
General and efficient strategy for erythrinan and homoerythrinan alkaloids:: Syntheses of (±)-3-demethoxyerythratidinone and (±)-erysotramidine
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DOI：
10.1021/ol0607185
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发表时间：
2006-05-25
期刊：
影响因子：
5.2
通讯作者：
Zhang, Shuyu
中科院分区：
文献类型：
--
作者：
Gao, Shuanhu;Tu, Yong Qiang;Zhang, Shuyu
针对芳香型和非芳香型赤藓红素及单赤藓红素生物碱，已经建立了一种通用而有效的策略。该方法包括一个关键的两步序列，酮与各种n -取代的碘乙酰胺的烷基化，然后是n -酰基胺离子促进的分子内环化，代表了赤藓红素和同赤藓红素生物碱的最短途径之一。作为应用，分别实现了(+/-)-3-去甲氧基赤藓苷酮的正式全合成和(+/-)-赤藓苷的正式全合成。
A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides followed by a N-acyliminium ion promoted intramolecular cyclization, and represents one of the shortest routes to erythrinan and homoerythrinan alkaloids. As the application, the formal total synthesis of ( +/-)-3-demethoxyerythratidinone and the total synthesis of ( +/-)-erysotramidine have been achieved, respectively.