Multi-step reaction with 12 steps
1.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 12 h / 20 °C
2.1: sodium periodate / tetrahydrofuran; water / 1 h / 20 °C
3.1: titanium tetrachloride; sparteine / dichloromethane / 0 °C
3.2: 1 h / 0 °C
4.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 18 h / 20 °C
5.1: lithium borohydride / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C
6.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C
7.1: chromium dichloride / tetrahydrofuran / 3 h / 20 °C
8.1: chromium dichloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); C17H26N2O6S / acetonitrile / 3 h / 20 °C
9.1: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 35 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 38.15 h / 0 - 30 °C
11.1: ammonium fluoride / methanol / 41 h / 20 - 40 °C
12.1: pyridine; Dess-Martin periodane / dichloromethane / 3 h / 20 °C
With
pyridine; chromium dichloride; ammonium fluoride; sodium periodate; osmium(VIII) oxide; lithium borohydride; 2,6-di-tert-butyl-pyridine; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); C17H26N2O6S; palladium 10% on activated carbon; water; hydrogen; titanium tetrachloride; Dess-Martin periodane; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; sparteine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;
3.1: Evans asymmetric aldol reaction / 3.2: Evans asymmetric aldol reaction / 6.1: Dess-Martin oxidation / 7.1: Takai olefination / 8.1: Nozaki-Hiyama-Kishi reaction / 12.1: Dess-Martin oxidation;
DOI:10.1021/ol300182r