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. 2016 Jul 8;21(7):892. doi: 10.3390/molecules21070892

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© 2016 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 15 — Total synthesis of FTC derivatives, dimethoxy-FTC (78) and Ko143 (77). Reagents and conditions: (a) (1) CH(OMe)₃; (2) Fmoc-HCl, pyridine, CH₂Cl₂; (3) piperidine, DMF; (4) Fmoc-l-pro-OH, CIP, DiPEA, MNP; (5) piperidine, THF; (b) (1) Hg(OOCCF₃)₂, KI, I₂, CH₂Cl₂, then Boc₂O, DMAP, MeCN; (2) Pd(OAc)₂, Ag₂CO₃, toluene; (3) Mg(ClO₄)₂, MeCN; (c) (1) 1-benzyl-2-methyl-(S)-1,2-aziridinedicarboxylate, ytterbium triflate, CH₂Cl₂; (2) H₂ balloon, MeOH, 10% Pd/C; (3) isovaleraldehyde, TFA, CH₂Cl₂; (4) N-Fmoc-5-t-butyl l-glutamic acid ester, diisopropylethylamine 2-chloro-1,3-dimethylimmidazolinium hexaflorophosphate, N-methylpyrrolidinone; (5) piperidine, THF.

Scheme 15 — Total synthesis of FTC derivatives, dimethoxy-FTC (78) and Ko143 (77). Reagents and conditions: (a) (1) CH(OMe)₃; (2) Fmoc-HCl, pyridine, CH₂Cl₂; (3) piperidine, DMF; (4) Fmoc-l-pro-OH, CIP, DiPEA, MNP; (5) piperidine, THF; (b) (1) Hg(OOCCF₃)₂, KI, I₂, CH₂Cl₂, then Boc₂O, DMAP, MeCN; (2) Pd(OAc)₂, Ag₂CO₃, toluene; (3) Mg(ClO₄)₂, MeCN; (c) (1) 1-benzyl-2-methyl-(S)-1,2-aziridinedicarboxylate, ytterbium triflate, CH₂Cl₂; (2) H₂ balloon, MeOH, 10% Pd/C; (3) isovaleraldehyde, TFA, CH₂Cl₂; (4) N-Fmoc-5-t-butyl l-glutamic acid ester, diisopropylethylamine 2-chloro-1,3-dimethylimmidazolinium hexaflorophosphate, N-methylpyrrolidinone; (5) piperidine, THF.