Multi-step reaction with 18 steps
1: 90 percent / Cs2CO3; CsI / acetonitrile / 3 h / 50 °C
2: NaBH4 / methanol / 0.25 h / 0 °C
3: 92 percent / DIPEA / 1,2-dichloro-ethane / 1 h / 60 °C
4: LiOH / H2O; methanol / 1 h / 60 °C
5: 80 percent / hexamethylphosphoric acid triamide / 0.5 h / 20 °C
6: 78 percent / TPAP; NMO / CH2Cl2 / 3 h / 20 °C
7: 75 percent / DIPEA; LiCl / acetonitrile / 72 h / 20 °C
8: Li-n-BuBH3 / tetrahydrofuran / 0.5 h / 20 °C
9: 78 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
10: 88 percent / LiAlH4 / diethyl ether / 0.25 h / 0 °C
11: PDC / zeolite / CH2Cl2 / 2 h / 20 °C
12: 65 percent / NH2NH2*H2O; NaOH / triethylene glycol / 2 h / 190 °C
13: TBAF / tetrahydrofuran / 12 h / 60 °C
14: 92 percent / MnO2 / CH2Cl2 / 48 h / 20 °C
15: 90 percent / (S)-BINAL-H / CH2Cl2; tetrahydrofuran / 1 h / -10 °C
16: 2M HCl / tetrahydrofuran / 3 h / 60 °C
17: NaBH4 / methanol / 15 h / 20 °C
18: 62 percent / pyridine; DMAP / CH2Cl2 / 5 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; manganese(IV) oxide; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; isocyanate de chlorosulfonyle; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (-)-(S)-BINAL-H; Li-n-BuBH3; tetrabutyl ammonium fluoride; caesium carbonate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; lithium chloride;
zeolite;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol;
1: Alkylation / 2: Reduction / 3: Alkylation / 4: Ring cleavage / 5: Esterification / 6: Oxidation / 7: Cyclization / 8: Reduction / 9: Substitution / 10: Reduction / 11: Oxidation / 12: Reduction / 13: Hydrolysis / 14: Oxidation / 15: Reduction / 16: Hydrolysis / 17: Ring cleavage / 18: Acylation;
DOI:10.7164/antibiotics.51.602