Multi-step reaction with 15 steps
1.1: 83 percent / t-BuCOOH; Ti(i-PrO)4; (+)-diethyl tartrate / 4 Angstroem molecular sieves / CH2Cl2 / -20 °C
2.1: SO3*py; Et3N; DMSO / CH2Cl2 / 20 °C
3.1: tetrahydrofuran / -40 °C
4.1: NaAlH2(OCH2CH2OMe) / diethyl ether / -20 - 0 °C
4.2: 90 percent / aq. NaIO4 / tetrahydrofuran / 20 °C
5.1: 91 percent / TsOH / dimethylformamide / 20 °C
6.1: OsO4; (DHQD)2PHAL; K3[Fe(CN)6] / K2CO3; MeSO2NH2 / H2O; 2-methyl-propan-2-ol / 0 °C
7.1: SO3*py; Et3N; DMSO / 20 °C
8.1: (+)-camphorsulfonic acid / methanol / 3 h / 20 °C
8.2: 84 percent / (+)-camphorsulfonic acid / toluene / 48 h / 20 °C
9.1: pyridine / CH2Cl2 / 0 - 20 °C
10.1: 2,6-lutidine / CH2Cl2 / 0 °C
11.1: DIBAL-H / tetrahydrofuran / -78 °C
12.1: 91 percent / I2; PPh3; imidazole / tetrahydrofuran / 20 °C
13.1: 83 percent / n-BuLi; HMPA / tetrahydrofuran / -78 °C
14.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C
15.1: 89 percent / TBAF / tetrahydrofuran / 0 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; n-butyllithium; pyridine-SO3 complex; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; (+)-10-camphorsulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); Trimethylacetic acid;
methanesulfonamide; 4 A molecular sieve; potassium carbonate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Sharpless epoxidation;
DOI:10.1002/anie.200461802