Synthesis of (-)-muricatacin.

Synthesis of (-)-muricatacin.
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(-)-muricatacin 的合成。

DOI:
10.1271/bbb.57.1028
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发表时间:
1993
期刊:
Bioscience, biotechnology, and biochemistry
影响因子:
--
通讯作者:
T. Oritani
T. Oritani
中科院分区:
--
文献类型:
--
作者:
H. Makabe;A. Tanaka;T. Oritani

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介绍了以1-溴十二烷和2-戊烷-1-醇为原料合成(-)-穆里卡星的方法。由1-溴十二烷(2)和2-戊烷-1-醇(3)制备的2-戊烷-1-醇(4),经过两步反应顺序,6依次进行甲酰化、碘化、与乙酸锂叔丁酯扩链、酸催化环化得到(-)-穆里卡塔星(1a)。再结晶得到光学纯净的1a。
The synthesis of (-)-muricatacin starting from 1-bromododecane and 2-pentyn-1-ol is described. 2-Pentadecyn-1-ol (4), which was prepared from 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy alcohol 6 through a two-step reaction sequence, 6 being successively submitted to tosylation, iodination, chain extension with tert-butyl lithioacetate, and acid-catalyzed cyclization to give (-)-muricatacin (1a). Recrystallization afforded optically pure 1a.