Multi-step reaction with 18 steps
1.1: Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2.1: LiCl; i-PrNEt2 / acetonitrile / 16 h / 20 °C
3.1: enriched AD-mix-β; MeSO3NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C
4.1: H2; NaHCO3 / Pd(OH)2/C / methanol / 20 h / 20 °C
5.1: Ph3CBF4 / tetrahydrofuran / 2 h / 0 °C
6.1: DIBAL-H / CH2Cl2 / 0.5 h / -78 °C
6.2: Ba(OH)2 / tetrahydrofuran; H2O / 16 h / 20 °C
7.1: AcOH / tetrahydrofuran; H2O / 48 h / 20 °C
7.2: 86 percent / KOH / methanol / 24 h / 20 °C
8.1: toluene / 2 h / 120 °C
9.1: tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH2Cl2 / 0.5 h / 20 °C
10.1: Et3N / diethyl ether / 2.5 h / -78 °C
11.1: diethyl ether / 16 h / -78 - -20 °C
11.2: H2O2 / methanol; H2O / 2 h / 0 - 20 °C / pH 7
12.1: PPTS / methanol / 1 h / 20 °C
13.1: imidazole; Et3N / dimethylformamide / 16 h / 20 °C
14.1: OsO4; H2O; Me3NO / acetone / 16 h / 20 °C
14.2: Pb(OAc)4; Na2CO3 / CH2Cl2 / 0.67 h / 0 °C
15.1: Et3N / diethyl ether / 1.5 h / -78 - -40 °C
16.1: diethyl ether / 16 h / -78 °C
16.2: H2O2 / methanol; H2O / 2.5 h / 0 °C / pH 7
17.1: 93 percent / imidazole / dimethylformamide / 3 h / 20 °C
18.1: Zn; TiCl4; PbI2 / tetrahydrofuran; CH2Cl2 / 4 h / 20 °C
With
1H-imidazole; osmium(VIII) oxide; tetrapropylammonium perruthennate; sulfamic acid methyl ester; N,N-diethyl-N-isopropylamine; trimethylamine-N-oxide; enriched AD-mix-β; water; hydrogen; trityl tetrafluoroborate; pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; lithium chloride; lead(II) iodide; zinc;
palladium dihydroxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
1.1: Dess-Martin oxidation / 2.1: Horner-Wadsworth-Emmons olefination / 3.1: Sharpless dihydroxylation / 6.2: Horner-Wadsworth-Emmons olefination / 7.1: hetero-Michael cyclization / 8.1: Petasis methylenation;
DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H