fredericamycin A synthesis

7synthesis methods

Product Name:fredericamycin A
CAS Number:80455-68-1
Molecular formula:C30H21NO9
Molecular Weight:539.49

6H-Cyclopent[g]isoquinoline-3-carboxylic acid, 1-ethoxy-7,8-dihydro-9-hydroxy-8-oxo-, ethyl ester

141903-31-3
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80455-68-1
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Yield:-

Steps:

Multi-step reaction with 16 steps
1: 93 percent / K₂CO₃, Bu₄NI / dimethylformamide / 6 h / 25 °C
2: t-BuOK, EtOH / CH₂Cl₂ / 7 h / -67 - 25 °C
3: 68 percent / Et₃N, DMAP
4: 5 percent / Dibal-H / tetrahydrofuran; toluene / 3 h / -78 °C
5: 2.) I₂ / 1.) THF, hexane, from -78 deg C to 25 deg C, 12 h, 2.) CH₂Cl₂, 25 deg C, 5 d
6: 1.) Dibal-H, 2.) 1.0 M aq. phosphate buffer / 1.) toluene, -30 deg C, 1 h, 2.) toluene, 25 deg C, 20 min
7: tetrahydrofuran / 2 h / -78 - 0 °C
8: imidazole / dimethylformamide / 22 h / 25 °C
9: 35 percent / Ac₂O / heptane / 47 h / 50 °C
10: 52 percent / K₂CO₃, Bu₄NI / acetone / 53 h / 25 °C
11: Bu₄NF / tetrahydrofuran / 10.5 h / 50 °C
12: DMSO, TFAA / CH₂Cl₂ / 1 h / -78 °C
13: DBU / CH₂Cl₂ / 20 h / -78 - 25 °C
14: 1.) TFAA, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, 25 deg C, 30 min
16: 1.) BBr₃, 2.) air, 3.) TsOH, NaBr