Journal of Organic Chemistry p. 4909 - 4913 (1985)
Update date:2022-08-03
Topics:
Jung, Michael E.
Rohloff, John C.
A new method for the conversion of optically active diketopiperazines (cyclo-dipeptides) into optically pure piperazines is described.Due to poor solubility of certain cyclo-dityrosine derivatives, the usual method using lithium aluminum hydride reaction was problematic, giving racemization under forcing conditions.However, the use of borane/tetrahydrofuran for this diketopiperazine to piperazine reduction proceeded well, affording high yields of optically pure materials.In this manner several mixed cyclo-dityrosine derivatives 9a-d were transformed into the piperazines 10a-d, potentially useful intermediates for the synthesis of the antibiotic alkaloids, piperazinomycin (1) and herquline (2).Finally, the naturally occuring alkaloid isolated from Zanthoxylum arborescens, 7b was prepared by this route.
View MoreShanghai Forever Synthesis Co.,Ltd.
Contact:021-61124658
Address:Zhoukang Road,Pudong New District,Shanghai,China
Shenzhen Sunrising Industry Co., ltd.
Contact:+86 755 86571158 / 86571159 / 86571160
Address:2108 ZHENYE INT. BUSINESS CENTER,NO.3101-90 QIANHAI RD, NANSHAN,SHENZHEN, CHINA
Shanghai Witshoot Internet Technology Co Ltd
Contact:+86-21-66390020
Address:Room 419, No.285 Luochuan Road (E)
Shanghai Sharing technologies Co., Ltd.
Contact:86-021-66787223
Address:No11, Lane 225, Jinxiang Road,Pudong district
Changsha Huajing Powdery Material Technological Co., Ltd.
Contact:86-731-88879686
Address:Building 2, West Garden, Main Campus of Central South University, Changsha, Hunan Province, China
Doi:10.1002/ardp.19763090408
(1976)Doi:10.1021/ja00863a029
(1962)Doi:10.1081/SCC-120030689
(2004)Doi:10.1021/ja01678a043
()Doi:10.1039/c9ob00901a
(2019)Doi:10.1021/jo00883a002
(1976)