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ChemicalBook CAS DataBase List PINANE THROMBOXANE A2
71111-01-8

PINANE THROMBOXANE A2 synthesis

3synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 9 steps
1: 1.) NaH / 1.) DMF, RT, 5 h, 2.) DMF, 80 deg C, 4 h
2: 1.) 9-BBN, 2.) lithium trimethoxyaluminum hydride / 1.) THF, methanol, reflux, 30 h, 2.) THF, methanol, 0 deg C, 1 h
3: p-toluenesulfonic acid / toluene / Heating
4: 12.1 g / liquid NH3, sodium / diethyl ether / 1 h / -78 °C
5: pyridinium dichromate / CH2Cl2 / 24 h / Ambient temperature
6: 1.) butyllithium / 1.) DMSO, pentane, RT, 15 min, 2.) DMSO, pentane, RT, overnight
7: aq. HCl / dioxane / 40 °C
8: 1.) NaH / 1.) THF, from 0 deg C to 25 deg C, 1 h, 2.) THF, a) 0 deg C, 0.5 h, b) 25 deg C, 2.5 h
9: 55 mg / aluminum isopropoxide, 2-propanol / toluene / 3.5 h / Heating

References:

Wilson;Peesapati;Jones;Hamilton [Journal of Medicinal Chemistry,1982,vol. 25,# 5,p. 495 - 500]