Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir
Posted on 2017-10-20 - 00:48
A practical and asymmetric synthesis
of a functionalized trans-cyclopropoxy building block
for the preparation of
the HCV NS3/4a protease inhibitor grazoprevir is reported. Intramolecular
SN2 displacement–ring closure, followed by a Baeyer–Villiger
oxidation, yields the desired trans-cyclopropanol
with full control of diastereoselectivity. A terminal alkyne is then
effectively installed using LiNH(CH2)2NEt2. Starting from (S)-epichlorohydrin, the
cyclopropoxy building block is prepared in 51% overall yield with
>99.8% optical purity without isolation of any intermediates.
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Xu, Feng; Zhong, Yong-Li; Li, Hongming; Qi, Ji; Desmond, Richard; Song, Zhiguo J.; et al. (2017). Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02867
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AUTHORS (11)
FX
Feng Xu
YZ
Yong-Li Zhong
HL
Hongming Li
JQ
Ji Qi
RD
Richard Desmond
ZS
Zhiguo J. Song
JP
Jeonghan Park
TW
Tao Wang
MT
Matthew Truppo
GH
Guy R. Humphrey
RR
Rebecca T. Ruck