Total Synthesis of (-)-Nakadomarin A
Total Synthesis of (-)-Nakadomarin A
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DOI：
10.1021/ja404673s
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发表时间：
2013-06-26
影响因子：
15
通讯作者：
Evans, David A.
中科院分区：
文献类型：
--
作者：
Bonazzi, Simone;Cheng, Bichu;Evans, David A.
报道了多环生物碱（-）-nakadomarin A（1）的收敛合成。该合成计划确定了大环内酰胺4作为重要的中间体之一（八步）。另一个合成子（五步）是双环[6.3.0]内酰胺5，含有一个单一的立构中心，在组装过程中控制所有后续的立体化学。甲硅烷基三氟甲磺酸酯促进的级联4和5被用来组装除了C5-C6键以外的大部分生物碱骨架。然后在一个额外的步骤中完成了Nakadomarin的合成。
The convergent synthesis of the polycyclic alkaloid (-)-nakadomarin A (1) is reported. The synthesis plan identified macrocyclic lactam 4 as one of the important synthons (eight steps). The other synthon (five steps) was bicyclo[6.3.0] lactam 5 containing a single stereocenter that controlled all of the subsequent stereochemistry during the assembly process. A silyl triflate-promoted cascade of 4 and 5 was used to assemble the bulk of the alkaloid skeleton with the exception of the C5-C6 bond. The nakadomarin synthesis was then completed in one additional step.