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. Author manuscript; available in PMC: 2019 Apr 19.
Published in final edited form as: Org Chem Front. 2017 Feb 9;4(6):995–1004. doi: 10.1039/C7QO00052A

Scheme 1.

Scheme 1.

Preparation of Tetrapeptide Fragment 8. Reagents and conditions: (a) NaH, MeI, THF; (b) L-Pro-OMe, HATU, DIPEA, DCM, 62% (2 steps); (c) (1) TFA, DCM; (2) Boc-Gly, HATU, DIPEA, DCM, 80% (2 steps); (d) (1) TFA, DCM; (2) Boc-Val-OH, HOBt, EDCI, DMF, 62% (2 steps).