Total synthesis of a novel immunosuppressant, myriocin (thermozymocidin, ISP-I), and Z-myriocin.
Total synthesis of a novel immunosuppressant, myriocin (thermozymocidin, ISP-I), and Z-myriocin.
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一种新型免疫抑制剂，多球菌素（thermozymocidin，ISP-I）和 Z-多球菌素的全合成。
DOI：
10.1248/cpb.42.994
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发表时间：
1994
影响因子：
1.7
通讯作者：
N. Murakami
中科院分区：
文献类型：
--
作者：
M. Yoshikawa;Y. Yokokawa;Y. Okuno;N. Murakami
以2-脱氧-D-葡萄糖为原料，合成了具有免疫抑制和抗真菌活性的多球壳菌素（myriocin，ISP-I）及其类似物Z-多球壳菌素（Z-myriocin）。该合成途径包括通过使用改进的Darzen反应作为其关键步骤，从异亚丙基六元酮立体选择性地形成多球壳菌素和Z-多球壳菌素中的手性α，α-二取代的氨基酸结构。
Myriocin (thermozymocidin, ISP-I), which was known to exhibit several interesting biological properties such as potent immunosuppressive and antifungal activities, and a new analog Z-myriocin were synthesized from 2-deoxy-D-glucose. This synthetic pathway comprises a stereoselective formation of the chiral alpha, alpha-disubstituted amino acid structure in myriocin and Z-myriocin from the isopropylidene six-membered ketone by using a modified Darzen reaction as its key step.