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Search for "drug manufacturing" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Modern synthetic pathways towards eribulin and its subunits

Sebastian Dominik Graf

Beilstein J. Org. Chem. 2026, 22, 495–526, doi:10.3762/bjoc.22.37

eribulin are summarized. Keywords: breast cancer; drug manufacturing; eribulin; Halaven; total synthesis; Introduction Eribulin (1) is a truncated derivative of halichondrin B (2), a complex natural product originally isolated from the marine sponge Halichondria okadai (Figure 1) [1][2][3][4][5]. Already

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Graphical Abstract

Figure 1: Eribulin with common synthetic precursor fragments and halichondrin B.

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Scheme 1: Overview of the industrial process pathway for the large-scale production of the mesylate salt of 1...

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Scheme 2: Synthesis of 22. (a) i. 2,2-dimethoxypropane, p-TsOH, MeOH, 65 °C; ii. NaBH₄, MeOH, rt; (b) i. NaH,...

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Scheme 3: Synthesis of 27. (a) i. NaH, BnBr, THF, rt; ii. iodobenzoic acid, MeCN, 80 °C; iii. (EtO)₂POCH₂COOE...

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Scheme 4: Synthesis of 31 and 33. (a) i. MMTrCl, iPr₂NEt, DCM, rt; ii. K₂CO₃, MeOH, DCM, rt; iii. TBDMSCl, im...

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Scheme 5: Synthesis of 1. (a) CrCl₂, 37, 38, 39 (proton sponge), LiCl, Mn, ZrCp₂Cl₂, MeCN, EtOAc; (b) SrCO₃, t...

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Scheme 6: Synthesis of 45. Above: Reaction conditions: (a) methoxyacetic acid, BF₃·OEt₂, DCM, −30 °C; (b) Pd(...

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Scheme 7: Synthesis of 64. Reaction conditions: (a) i. acetone, I₂, rt; ii. vinylmagnesium bromide, THF, −20 ...

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Scheme 8: Synthesis of 79. Above: Reaction conditions: (a) i. K₂CO₃, MeOH, 60 °C; ii. 2,2-dimethoxypropane, H₂...

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Scheme 9: Synthesis of 92. Reaction conditions: (a) TESCl, imidazole, DCM, 0 °C to rt; (b) i. oxalyl chloride...

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Scheme 10: Synthesis of 104. Above: Reaction conditions: (a) cyclohexanone, p-TsOH, toluene, 110 °C, crystalli...

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Scheme 11: Synthesis of 117. (a) i. acetone, CuSO₄, rt; ii. H₂O₂, K₂CO₃, H₂O, rt; iii. EtI, MeCN, 70 °C; (b) i...

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Scheme 12: Synthesis of 121. Reaction conditions: (a) i. TBDPSCl, imidazole, DMF, rt; ii. O₃, DCM, −78 °C; iii...

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Scheme 13: Synthesis of 131. (a) i. 2,2-dimethoxypropane, p-TsOH, MeOH, 60 °C; ii. LiAlH₄, THF, 0 °C to rt; (b...

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Scheme 14: Synthesis of 143. (a) i. I₂, PPh₃, imidazole, DCM; ii. HMPA, CuI, vinylmagnesium bromide, THF, −20 ...

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Scheme 15: Modified synthesis of 104. Reaction conditions: (a) (EtO)₂POCH₂COOEt, KOt-Bu, THF, 15 °C; (b) TBAF,...

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Scheme 16: Synthesis of 161. Reaction conditions: (a) crotyl bromide, Sn, TBAI, NaI, DMF/H₂O, rt; (b) NaH, BnB...

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Scheme 17: Synthesis of 169. Reaction conditions: (a) i. Co₂(CO)₈, BF₃·Et₂O, DCM, 23 °C; ii. CAN, acetone, 0 °...

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Scheme 18: Synthesis of 181. Reaction conditions: (a) i. Co₂(CO)₈, BF₃·Et₂O, DCM, 23 °C; ii. (NH₄)₂Ce(NO₃)₆, a...

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Scheme 19: Synthesis of 186. Reaction conditions: (a) NEt₃, LiCl, MeCN, 0–23 °C; (b) HF·pyridine, MeCN, 23 °C;...

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Scheme 20: Modified synthesis of 181. Reaction conditions: (a) i. Ni(cod)₂, P(n-Bu)₃, Et₃SiH, THF, 23 °C; ii. ...

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Scheme 21: Synthesis of 200. Reaction conditions: (a) i. Co₂(CO)₈, DCM, 23 °C; ii. BF₃·Et₂O, 0 °C; iii. (NH₄)₂...

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Scheme 22: Modified synthesis of 186. Reaction conditions: (a) DDQ, 2,6-di-t-Bu-4-hydroxytoluene, hv, MeCN, 23...

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Scheme 23: Synthesis of 1. Reaction conditions: (a) i. CrCl₂, NiCl₂, 206, NEt₃, THF, 23 °C; ii. DBU, toluene, ...

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Scheme 24: Synthesis of 217. Above: Reaction conditions: (a) TBDPSCl, imidazole, DCM, 0–5 °C. (b) m-CPBA, DCM,...

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Scheme 25: Synthesis of 231. Reaction conditions: (a) i. AcCl, MeOH, 0 °C to rt; ii. TrCl, pyridine, 50 °C; (b...

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Scheme 26: Synthesis of 239. Reaction conditions: (a) i. Boc₂O, K₂CO₃, THF, rt; ii. Ru(acac)₃, NaBrO₃, EtOAc, H...

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Scheme 27: Synthesis of 247. Reaction conditions: (a) NCS, 248, MeCN, 0 °C to rt; (b) LDA, 249, THF, −78 °C; (...

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Scheme 28: Synthesis of 255. Reaction conditions: (a) i. LiHMDS, THF, −78 °C to rt; ii. m-CPBA, DCM, −78 °C to...

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Scheme 29: Synthesis of 261. Reaction conditions: (a) allyltrimethylsilane, TiCl₄, DCM −78 °C; (b) LiBH₄, EtOH...

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Scheme 30: Synthesis of 265. Reaction conditions: (a) (R,R)-Ru-cat (0.2 mol %), DCM, NEt₃, HCOOH, rt; (b) TBAF...

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Scheme 31: Synthesis of 272. Reaction conditions: (a) LDA, THF, −78 °C; (b) DMP, NaHCO₃, DCM, 0 °C to rt; (c) (...

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Scheme 32: Synthesis of 292. Reaction conditions: (a) TsCl, NEt₃, DCM, rt; (b) K₂CO₃, MeOH, 45 °C; (c) vinylma...

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Scheme 33: Synthesis of 296. Reaction conditions: (a) 171 (see Scheme 17), Cr-cat, CoPc (see Scheme 17), Mn, NEt₃·HCl, LiCl, TMS...

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Scheme 34: Synthesis of 299. Reaction conditions: (a) 172 (see Scheme 17), CrCl₂, NEt₃, NiCl₂, THF, rt; (b) KHMDS, THF,...

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Scheme 35: Synthesis of 305. Reaction conditions: (a) i. p-TsOH, MeOH, 40 °C; ii. MeLi, LiBr, THF, −25 °C; (b)...

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Scheme 36: Synthesis of 1. Reaction conditions: (a) i. 41 (see Scheme 6), LDA, THF, −78 °C; ii. DMP, NaHCO₃, DCM, rt; ...

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Scheme 37: Synthesis of 324. Reaction conditions: (a) i. acetone, CuSO₄, rt; ii. H₂O₂ (30%), K₂CO₃, rt; iii. E...

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Album

Review

Published 19 Mar 2026

Full text

Organocatalysis

Benjamin List

Beilstein J. Org. Chem. 2012, 8, 1358–1359, doi:10.3762/bjoc.8.156

on the other hand. There are additional aspects that belong to the field and that are being actively researched, including supported catalysts, organocatalysis in unusual reaction media, and applications in polymerizations, in total synthesis and drug-discovery, as well as in drug manufacturing

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Editorial

Published 23 Aug 2012

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