Multi-step reaction with 10 steps
1.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 - -45 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere
3.2: 12 h / -78 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere
5.1: lithium borohydride / methanol; diethyl ether / 12 h / 0 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere
7.1: dichloromethane / 55 °C / Inert atmosphere
8.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.58 h / -78 °C / Inert atmosphere
8.2: 12 h / 20 °C / Inert atmosphere
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
10.2: 2 h / -105 - -78 °C / Inert atmosphere
With
2,6-dimethylpyridine; lithium borohydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; t-butyldimethylsiyl triflate; water; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Aldol Addition / 3.2: |Aldol Addition / 7.1: |Wittig Olefination / 10.2: |Aldol Condensation;
DOI:10.1021/ol5011278