ChemicalBook CAS DataBase List 2,7,11-cembratriene-4,6-diol

2,7,11-cembratriene-4,6-diol synthesis

4synthesis methods

Product Name:2,7,11-cembratriene-4,6-diol
CAS Number:57605-80-8
Molecular formula:C20H34O2
Molecular Weight:306.48

2,6,10-Dodecatrien-1-ol, 12-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,7,11-trimethyl-, (2E,6E,10E)-

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Yield:-

Steps:

Multi-step reaction with 18 steps
1: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -78 °C
2: 96 percent / diethyl ether; toluene / 6 h / -20 °C
3: 96 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature
4: 98 percent / 1.1M n-Bu₄NF / tetrahydrofuran / 5 h / 0 °C
5: 84 percent / LiCl, methanesulfonyl chloride, 2,6-lutidine / dimethylformamide / 2.5 h / 0 °C
6: 83 percent / 1.)n-BuLi, 1,10-phenanthroline / tetrahydrofuran / 1.)-78 deg C, 1 h, 2.)0 deg C, 0.5 h
7: 1.)EtMgBr, 1,10-phenanthroline / 1.)THF, HMPA, 0 deg C, 5 min., 2.)reflux, 4 h
8: 85 percent / pyridinium p-toluenesulfonate / methanol / 16 h / Ambient temperature
9: 80 percent / triethylamine, DMAP / CH₂Cl₂ / Ambient temperature
10: 90 percent / n-BuLi / pentane; tetrahydrofuran / 3 h / -78 °C
11: 96 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -78 °C
12: 86 percent / CuI / tetrahydrofuran / 0 °C
13: 96 percent / 0.1M DIBAH / tetrahydrofuran; hexane / 1 h / -78 °C
14: 69 percent / H₂ / (Ph₃P)3RhCl / ethanol; benzene / 4 h
15: 88 percent / 3.9 M t-BuOOH / VO(acac)2 / toluene; 2,2,4-trimethyl-pentane / 1 h / Ambient temperature
16: 92 percent / CH₂Cl₂; pyridine / 18 h / 0 °C
17: 92 percent / 1.1M Bu₄NF / tetrahydrofuran / 2 h / 0 °C
18: 75 percent / Na, NH₃-gas / tetrahydrofuran / -40 °C

References:

Marshall;Robinson;Lebreton [Journal of Organic Chemistry,1990,vol. 55,# 1,p. 227 - 239]

2,6,10-Dodecatrienal, 12-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,7,11-trimethyl-, (E,E,E)- (9CI)

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References

5,9,13-Pentadecatrien-1-yn-4-ol, 15-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6,10,14-trimethyl-, (5E,9E,13E)-

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57605-80-8
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References

2H-Pyran, 2-[[12-chloro-3,7,11-trimethyl-1-(2-propynyl)-2,6,10-dodecatrienyl]oxy]tetrahydro-, (E,E,E)- (9CI)

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57605-80-8
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References