Problem 6. The following scheme details a retrosynthesis of Grazoprevir. Provide the details of how to couple the pieces shown into the final product using at least 2 of the C-C couplings listed in the upper left corner (i.e. you will provide two different syntheses, each using a different C-C coupling).

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Problem 6. The following scheme details a retrosynthesis of Grazoprevir. Provide the details of how to couple the
pieces shown into the final product using at least 2 of the C-C couplings listed in the upper left corner (i.e. you will
provide two different syntheses, each using a different C-C coupling).
Scheme 1. Retrosynthetic Analysis of Grazoprevir
HO₂C
R.
C-C coupling:
Sonogashira
Heck
Suzuki
Metathesis
2
NH Meo.
Grazoprevir (1)
↓↓
X = OH, CI
Y = Cl, alkenyl
3
Y
OMe
HO
SNAr
CO₂Me
Amidation
4
H₂N
N-Boc
5
Transcribed Image Text:Problem 6. The following scheme details a retrosynthesis of Grazoprevir. Provide the details of how to couple the pieces shown into the final product using at least 2 of the C-C couplings listed in the upper left corner (i.e. you will provide two different syntheses, each using a different C-C coupling). Scheme 1. Retrosynthetic Analysis of Grazoprevir HO₂C R. C-C coupling: Sonogashira Heck Suzuki Metathesis 2 NH Meo. Grazoprevir (1) ↓↓ X = OH, CI Y = Cl, alkenyl 3 Y OMe HO SNAr CO₂Me Amidation 4 H₂N N-Boc 5
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