Multi-step reaction with 10 steps
1.1: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2.5 h / 20 °C
2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C
2.2: 9.90 g / hydrogen peroxide; sodium hydroxide / tetrahydrofuran / 1.5 h / 20 °C
3.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 0.5 h / 0 °C
4.1: acetic acid / tetrahydrofuran; H2O / 20 °C
5.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH2Cl2 / 2 h / 20 °C
6.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C
7.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C
8.1: N,N'-bis(2,4,6-Me3C6H2CH2)-(S,S)-1,2-Ph2-1,2-diaminoethane; osmium tetroxide / CH2Cl2 / 2 h / -90 °C
8.2: 85 percent / NaHSO3 / tetrahydrofuran; H2O / 2 h / Heating
9.1: 86 percent / camphorsulfonic acid / benzene / 36 h / 20 °C
10.1: 83 percent / sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 50 °C
With
osmium(VIII) oxide; dipyridinium dichromate; pyridine-SO3 complex; 4 A molecular sieve; camphor-10-sulfonic acid; 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: Addition / 2.1: hydroboration / 2.2: Oxidation / 3.1: Oxidation / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: Methylation / 7.1: Addition / 8.1: Oxidation / 8.2: Ring cleavage / 9.1: Cyclization / 10.1: Etherification;
DOI:10.1021/jo990988j