Multi-step reaction with 12 steps
1.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
1.2: 71 percent / tetrahydrofuran / 0 - 20 °C
2.1: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2.5 h / 20 °C
3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C
3.2: 9.90 g / hydrogen peroxide; sodium hydroxide / tetrahydrofuran / 1.5 h / 20 °C
4.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 0.5 h / 0 °C
5.1: acetic acid / tetrahydrofuran; H2O / 20 °C
6.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH2Cl2 / 2 h / 20 °C
7.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C
8.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C
9.1: N,N'-bis(2,4,6-Me3C6H2CH2)-(S,S)-1,2-Ph2-1,2-diaminoethane; osmium tetroxide / CH2Cl2 / 2 h / -90 °C
9.2: 85 percent / NaHSO3 / tetrahydrofuran; H2O / 2 h / Heating
10.1: 86 percent / camphorsulfonic acid / benzene / 36 h / 20 °C
11.1: 83 percent / sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 50 °C
12.1: 77 percent / dimethyl sulfide; BF3*Et2O / CH2Cl2 / 0.33 h / 0 °C
With
osmium(VIII) oxide; dipyridinium dichromate; pyridine-SO3 complex; dimethylsulfide; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; (1S,2S)-1,2-diphenyl-N1,N2-bis(mesitylmethyl)ethane-1,2-diamine; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
1.1: Dehydrobromination / 1.2: methylenation; Wittig reaction / 2.1: Addition / 3.1: hydroboration / 3.2: Oxidation / 4.1: Oxidation / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: Methylation / 8.1: Addition / 9.1: Oxidation / 9.2: Ring cleavage / 10.1: Cyclization / 11.1: Etherification / 12.1: Hydrolysis;
DOI:10.1021/jo990988j