Photochemistry of ergosterol and synthesis of lumisterol2

ORGN 501

Bao-Wen Zhang, g203@mail.ipc.ac.cn, Xue-Song Wang, Xue-Xin Cheng, and Yong-Yong Liu. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100080, China

The photoisomerization of ergosterol to previtamin D2, followed by thermal conversion to vitamin D2 (VD2), has been studied intensively. Lumisterol2 is one of the byproducts, which is an important intermediate for preparation of hormone analogs such as 6-dehydro-9(beta),10(alpha)- progesterone.

To maximize the yield of lumisterol2, a detailed study of photochemistry of ergosterol has been carried out, which shows that one pot direct irradiation procedure could be applied on a preparative scale. The irradiation of ergosterol solution with >283 nm light gave 17.2% previtamin2, 25% lumisterol2, 1.8% tachysterol2, and 56% ergosterol (HPLC). Recrystallization from methanol gave pure lumisterol2 in the yield of 75% based on the consumed ergosterol. The isolation procedure should be performed below 30ºC to prevent previtamin2 from going to VD2, because we found that lumisterol2 and VD2 can form 1:1 complex, which would cause a difficulty in lumisterol2 isolation and lower the yield of lumisterol2.