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. 2024 Aug 6;10(9):1703–1717. doi: 10.1021/acscentsci.4c00776

Scheme 1. Total Synthesis of Laterocidine.

Scheme 1

(a) Fmoc-AA-OH (3 equiv), HCTU (3 equiv), DIPEA (6 equiv), in DMF 50 min; (b) 20% piperidine/DMF (1 × 5 min, 1 × 10 min); (c) Alloc-Gly-OH (5 equiv), DIC (5 equiv), DMAP (0.3 equiv) in DMF; (d) palladium tetrakis(triphenylphosphine) (0.1 equiv), PhSiH3 (10 equiv), in DCM 40 min; (e) 10% HFIP in DCM (1 × 30 min, 1 × 5 min); (f) DPPA, DIEA in DMF 6 h; (g) TFA:TIPS:DODT:H2O (92.5:2.5:2.5:2.5) 90 min. HPLC and mass spectrum of peptides 1, 8, and 10. O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HCTU), 1,1,1,3,3,3-hexafluoro isopropanol (HFIP), dichloromethane (DCM) diphenylphosphoryl azide (DPPA), di-isopropyl carbodiimide (DIC), dimethylaminopyridine (DMAP), diisopropylethylamine (DIEA), dimethylformamide (DMF), triisopropylsilane (TIPS), 3,6-dioxa-1,8-octanedithiol (DODT), and trifluoroacetic acid (TFA).