A Carbohydrate-Based Approach for the Total Synthesis of (-)-Dinemasone B, (+)-4a-epi-Dinemasone B, (-)-7-epi-Dinemasone B, and (+)-4a,7-Di-epi-dinemasone B
A Carbohydrate-Based Approach for the Total Synthesis of (-)-Dinemasone B, (+)-4a-epi-Dinemasone B, (-)-7-epi-Dinemasone B, and (+)-4a,7-Di-epi-dinemasone B
复制标题
基于碳水化合物的 (-)-迪奈马松 B、( )-4a-epi-迪奈马松 B、(-)-7-epi-迪奈马松 B 和 ( )-4a,7-Di-epi- 的全合成方法
DOI：
10.1021/jo4015694
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发表时间：
2013-09-20
影响因子：
3.6
通讯作者：
Li, Zhongjun
中科院分区：
文献类型：
--
作者：
Xue, Xiaochao;Yin, Zhaojun;Li, Zhongjun
（-）-地松B由克罗恩及其同事从内生真菌Dinemasporium strigosum的培养物中分离，并显示出有希望的抗微生物活性。本文描述了（-）-地米松B、（+）-4 α-表-地米松B、（-）-7-表-地米松B和（+）-4 α，7-二-表-地米松B的首次全合成。并测定了它们的绝对构型。开发的合成功能的立体选择性还原C-糖苷酮，内酯化，和E-烯化醛从D-葡萄糖开始。
(-)-Dinemasone B was isolated by Krohn and co-workers from a culture of the endophytic fungus Dinemasporium strigosum and has shown promising antimicrobial activity. Described herein is the first total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B. Their absolute configurations were also determined. The developed synthesis features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from D-glucose.