A procedure for the stereospecific synthesis of drospirenone has been developed. The key steps included the stereospecific reduction of the C7-tertiary alcohol with ZnI2/Et3SiH, a novel mild and stereospecific tertiar...A procedure for the stereospecific synthesis of drospirenone has been developed. The key steps included the stereospecific reduction of the C7-tertiary alcohol with ZnI2/Et3SiH, a novel mild and stereospecific tertiary alcohol reduction system, and the tandem oxidation/cyclopropanation reactions.展开更多
The Pd(PPh_3)_4-catalyzed coupling reaction of alkenyl-disiamylboranes with furfuryl chloride in the presence of t-BuOK afforded(E)-furfurylalkenes stereospecifically in good yields.
Alkyl glucoside 1 and aryl glycosides 2-4 were highly stereospecifically synthesized over 4-6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprote...Alkyl glucoside 1 and aryl glycosides 2-4 were highly stereospecifically synthesized over 4-6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β-configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time.展开更多
基金Acknowledgement This research was financially supported in part by the China Postdoctoral Science Foundation and the Na- tional Basic Research Program of China （Nos. 2010CB833200, 2010CB833300）, the National Natural Science Foundation of China （Nos. 20832007, 21102167）, the Science and Technology Commission of Shanghai Municipality （No. 12DZ1930902） and the Knowledge Innovation Program of Chinese Academy of Sciences. We thank Zhejiangshenzhou Pharmaceutical Co., Ltd for providing starting materials.
文摘A procedure for the stereospecific synthesis of drospirenone has been developed. The key steps included the stereospecific reduction of the C7-tertiary alcohol with ZnI2/Et3SiH, a novel mild and stereospecific tertiary alcohol reduction system, and the tandem oxidation/cyclopropanation reactions.
基金Project supported by the National Natural Science Foundation of China
文摘The Pd(PPh_3)_4-catalyzed coupling reaction of alkenyl-disiamylboranes with furfuryl chloride in the presence of t-BuOK afforded(E)-furfurylalkenes stereospecifically in good yields.
基金Project supported by the National Natural Science Foundation of China （Nos. 20472025 and QT 20021001）.
文摘Alkyl glucoside 1 and aryl glycosides 2-4 were highly stereospecifically synthesized over 4-6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β-configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time.
