Multi-step reaction with 20 steps
1.1: 92 percent / EtAlCl2 / toluene
2.1: 89 percent / H(1+)
3.1: N-methylmorpholine-N-oxide / OsO4
4.1: NaIO4
5.1: 90 percent / m-chloroperbenzoic acid / CH2Cl2
6.1: 92 percent / H(1+)
7.1: 100 percent / K2CO3 / methanol
8.1: 90 percent / pyridinium chlorochromate; 4 Angstroem MS / CH2Cl2
9.1: Et3N
9.2: 89 percent / -78 °C
10.1: 73 percent / oxone / acetone
11.1: 79 percent / Al(Oi-Pr)3 / toluene
12.1: 96 percent / Et3N
13.1: 100 percent / -78 °C
14.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran
15.1: 86 percent / NaH / 80 °C
16.1: 85 percent / N-methylmorpholine-N-oxide / OsO4
17.1: 89 percent / NaIO4
18.1: 70 percent / H2 / Pd/C
19.1: 94 percent / NaBH4 / methanol
20.1: 98 percent / collidine / 0 °C
With
2,3,5-trimethyl-pyridine; Oxone; sodium tetrahydroborate; sodium periodate; 4 Angstroem MS; tetrabutyl ammonium fluoride; hydrogen; hydrogen cation; aluminum isopropoxide; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate;
palladium on activated charcoal; osmium(VIII) oxide; ethylaluminum dichloride;
In
tetrahydrofuran; methanol; dichloromethane; acetone; toluene;
1.1: Diels-Alder reaction / 5.1: Baeyer-Villiger oxidation / 11.1: Oppenauer ox. and Meerwein-Pondorf-Verley red.;
DOI:10.1016/S0040-4039(01)01802-0