Multi-step reaction with 17 steps
1.1: 96 percent / PDC / CH2Cl2 / 16 h
2.1: n-BuLi; i-Pr2NH / hexane; tetrahydrofuran / 0.75 h / -78 °C
2.2: 93 percent / hexane; tetrahydrofuran / 6 h / 20 °C
3.1: H2 / PtO2 / ethanol / 16 h
3.2: 99 percent / aq. HF / acetonitrile / 12 h
4.1: 96 percent / DIB; I2 / cyclohexane / sonicated
5.1: 62 percent / BF3*OEt2 / 0.83 h / -30 - 0 °C
6.1: 99 percent / K2CO3 / methanol / 2 h
7.1: 97 percent / diacetoxyiodobenzene; TEMPO / CH2Cl2; acetonitrile / 5 h
8.1: 98 percent / imidazole / dimethylformamide / 30 h
9.1: NaH / tetrahydrofuran / 1.17 h / 0 - 20 °C
9.2: 93 percent / tetrahydrofuran / 72 h
10.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 h
11.1: 81 percent / DIBAL-H / toluene; hexane / -80 °C
12.1: t-BuOK / benzene / 2 h / Heating
12.2: 71 percent / benzene / 12 h / 20 °C
13.1: tetrahydrofuran; diethyl ether / 4 h / 20 °C
13.2: 82 percent / tetrahydrofuran; diethyl ether / 12 h / -20 °C
14.1: 60 percent / aq. HF / acetonitrile / 3 h
15.1: 98 percent / H2 / Pd/C / ethyl acetate / 16 h
16.1: 90 percent / pyridinium dichromate / CH2Cl2 / 16 h
17.1: 96 percent / n-HexLi / hexane; tetrahydrofuran / 3 h / -78 - -20 °C
With
1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; dipyridinium dichromate; n-butyllithium; [bis(acetoxy)iodo]benzene; 4,4'-diiodobiphenyl; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; hydrogen; iodine; n-hexyllithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; diisopropylamine;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
9.1: Horner-Wadsworth-Emmons reaction / 12.2: Wittig reaction;
DOI:10.1021/jo0498664
![[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide](/Databaselist/images/loading.webp)
