Total synthesis of (±)-symbioimine
Total synthesis of (±)-symbioimine
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DOI：
10.1021/ol062333s
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发表时间：
2006-11-23
期刊：
影响因子：
5.2
通讯作者：
Snider, Barry B.
中科院分区：
文献类型：
--
作者：
Zou, Yefen;Che, Qinglin;Snider, Barry B.
（+/-）-共生亚胺（1）的合成仅需12步线性反应，总收率为8%。关键步骤是13 b与BF_3中心点Et_2O反应生成N-烷氧羰基二氢吡啶阳离子14 b，14 b发生分子内Diels-Alder反应生成加合物16 b，产率42%。16 b的N-Troc基团的裂解立体特异性地得到亚胺24 b。TBDMS醚的裂解和硫酸化提供（+/-）-共生亚胺（1）。
The synthesis of (+/-)- symbioimine (1) has been completed in only 12 linear steps in 8% overall yield. The key step is the treatment of 13b with BF3 center dot Et2O to generate N-carboalkoxydihydropyridinium cation 14b, which undergoes a novel stereospecific intramolecular Diels-Alder reaction to give adduct 16b in 42% yield. Cleavage of the N-Troc group of 16b afforded imine 24b stereospecifically. Cleavage of the TBDMS ethers and sulfation provided (+/-)-symbioimine (1).