Cryptotanshinone synthesis
- Product Name:Cryptotanshinone
- CAS Number:35825-57-1
- Molecular formula:C19H20O3
- Molecular Weight:296.36
Cryptotanshinone is the main fat-soluble extract of Salvia miltiorrhiza, with antitumor, antioxidant, anti-inflammatory, antibacterial and other activities. It can be obtained by Salvia miltiorrhiza as raw material, ultrasonic extraction with 95% ethanol, extraction and purification with NaHCO3 solution.
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Yield:-
Steps:
Multi-step reaction with 9 steps
1: 1.) n-BuLi, TMEDA / 1.) hexane, 45 deg C, 30 min, 2.) THF, 55-60 deg C, 20 h
2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C
3: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C
4: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
5: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
6: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
7: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
8: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
9: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
References:
Danheiser, Rick L.;Casebier, David S.;Firooznia, Fariborz [Journal of Organic Chemistry,1995,vol. 60,# 26,p. 8341 - 8350]
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