ChemicalBook CAS DataBase List Leptomycin B

Leptomycin B synthesis

9synthesis methods

Product Name:Leptomycin B
CAS Number:87081-35-4
Molecular formula:C33H48O6
Molecular Weight:540.73

4-Pentyn-2-ol, 3-methyl-1-(phenylmethoxy)-, (2R,3S)-

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Yield:-

Steps:

Multi-step reaction with 17 steps
1: 1.) nBuLi, iPr₂NH / 1.) THF, -78 deg C; 2.) THF, -60 deg C
2: H₂, quinoline / Pd/BaSO₄ / ethanol
3: benzene / Heating
4: DIBAL-H / CH₂Cl₂ / -78 °C
5: PPTS / benzene
6: 89 percent / lithium di-tert-butylbiphenyl / tetrahydrofuran / -78 °C
7: 1.) (COCl)2; 2.) Et₃N / 1.) DMSO, CH₂Cl₂; 2.) -78 deg C
8: 59 percent / LiCH₂S(O)CH₃ / toluene / -78 - 5 °C
9: Dowex HCR-W₂ / acetone; H₂O / 40 °C
10: Ag₂CO₃-celite / benzene / 50 °C
11: 89 percent / DDQ, CH₂Cl₂, tBuOH, buffer
12: 99 percent / Dess-Martin periodinane / CH₂Cl₂
13: 90 percent / LiCH₂S(O)CH₃ / toluene / -78 - 5 °C
14: 71 percent / Dess-Martin periodinane / CH₂Cl₂
15: 89 percent / HF*pyridine, pyridine / tetrahydrofuran
16: MnO₂ / benzene
17: NaClO₂, NaH₂PO₄, H₂O₂ / acetonitrile