trilobacin synthesis

9synthesis methods

Product Name:trilobacin
CAS Number:140224-67-5
Molecular formula:C37H66O7
Molecular Weight:622.9157

4-Octenoic acid, 8-(phenylmethoxy)-, ethyl ester, (4E)-

181803-05-4
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Yield:-

Steps:

Multi-step reaction with 21 steps
1: AD-mix-β, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
2: 1.) aq. KOH, 2.) aq. HCl / 1.) MeOH
3: TsOH / CH₂Cl₂ / 1 h / Ambient temperature
4: imidazole / dimethylformamide / 16 h / Ambient temperature
5: H₂ / Pd/C (10percent) / methanol; propionic acid / 24 h
6: PCC, celite / CH₂Cl₂ / 2 h
7: 1.) KN(SiMe₃)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h
8: Bu₄NF / dimethylformamide / 2 h / Ambient temperature
9: 1.) Re₂O₇, lutidine, 2.) TsOH / 1.) CH₂Cl₂, 4 h, 2.) dimethoxypropane, acetone, 1 h
10: PPH₃, DEAD / benzene / 16 h
12: CH₂Cl₂ / 1 h / -20 - 0 °C
13: TsOH / methanol; H₂O / 16 h / Ambient temperature
14: pyridine / 2 h / 100 °C
15: LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating
17: I₂, PPh₃, imidazole / CH₂Cl₂ / 1 h / Ambient temperature
18: NaHCO₃ / acetonitrile / 24 h / 45 °C
19: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h
20: H₂, Rh(PPh₃)3Cl / benzene; ethanol / 2 h / Ambient temperature
21: acetyl chloride / methanol; diethyl ether / 6 h / Heating

References:

Sinha, Subhash C.;Sinha, Anjana;Yazbak, Ahmad;Keinan, Ehud [Journal of Organic Chemistry,1996,vol. 61,# 22,p. 7640 - 7641]

2(5H)-Furanone, 3-[(2R,13R)-2,13-dihydroxy-13-[(2R,2'S,5R,5'R)-octahydro-5'-[(1R)-1-hydroxyundecyl][2,2'-bifuran]-5-yl]-8-tridecen-1-yl]-5-methyl-, (5S)-

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References

2(3H)-Furanone, dihydro-5-[(1R)-1-hydroxy-4-(phenylmethoxy)butyl]-, (5R)-

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References

2(3H)-Furanone, 5-[(1R)-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-(phenylmethoxy)butyl]dihydro-, (5R)-

303053-14-7
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References

4-Pentadecenoic acid, ethyl ester, (4E)-

59101-21-2
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References