Multi-step reaction with 10 steps
1.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Molecular sieve
2.1: silver(l) oxide; titanium tetrachloride; titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / dichloromethane; diethyl ether / 21 h / -15 - 4 °C / Inert atmosphere
3.1: acetic acid / tetrahydrofuran; water / 0.83 h / 55 °C
4.1: mercury(II) perchlorate hexahydrate / dichloromethane; water; acetonitrile / 0.75 h / 4 °C
5.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 2 h / 20 °C
5.2: 1.5 h / 20 - 50 °C
6.1: sodium periodate; potassium permanganate / tert-butyl alcohol / 1 h / 20 °C / pH 7.2
7.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 11.5 h / 4 °C
8.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 3 h / 20 °C
8.2: 5 h / 4 - 20 °C
9.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.67 h / 20 °C / Molecular sieve
10.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 4 °C
10.2: 3 h / -78 - -10 °C
With
pyridine; titanium(IV) isopropylate; potassium permanganate; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; mercury(II) perchlorate hexahydrate; 2,4,6-trichlorobenzoyl chloride; (S)-[1,1']-binaphthalenyl-2,2'-diol; titanium tetrachloride; pyridine hydrogenfluoride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; silver(l) oxide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;
1.1: |Ley Oxidation / 8.2: |Yamaguchi Lactonization;
DOI:10.3987/COM-12-S(N)8