1415237-38-5Relevant articles and documents
The manufacture of a homochiral 4-silyloxycyclopentenone intermediate for the synthesis of prostaglandin analogues
Henschke, Julian P.,Liu, Yuanlian,Huang, Xiaohong,Chen, Yungfa,Meng, Dechao,Xia, Lizhen,Wei, Xiuqiong,Xie, Aiping,Li, Danhong,Huang, Qiang,Sun, Ting,Wang, Juan,Gu, Xuebin,Huang, Xinyan,Wang, Longhu,Xiao, Jun,Qiu, Shenhai
, p. 1905 - 1916 (2012)
A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ recycling of the undesired enantiomer furnishing the desired homochiral alcohol in ≥99.5% ee. As a retort to the unsatisfactory coformation of about 8% at best of the trans-olefin in the Wittig reaction, a change to the order of several steps and the identification of a recrystallisable, amine salt derivative, 2, allowed the unwanted isomer to be controlled to as low as 0.2%.
