Synthesis and formation mechanism of ocotillol and its epimer

WANG Wenzhi; XU Yangrong; LI Xinli; YANG Jingjing; MENG Qingguo

doi:10.11665/j.issn.1000-5048.20160305

Journal of China Pharmaceutical University > 2016 > 47(3): 282-287. > DOI: 10.11665/j.issn.1000-5048.20160305

WANG Wenzhi, XU Yangrong, LI Xinli, YANG Jingjing, MENG Qingguo. Synthesis and formation mechanism of ocotillol and its epimer[J]. Journal of China Pharmaceutical University, 2016, 47(3): 282-287. DOI: 10.11665/j.issn.1000-5048.20160305

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Synthesis and formation mechanism of ocotillol and its epimer

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Ocotillol( 3 )and its epimer( 4 )have been synthesized from 20(S)-protopanaxatriol ［20(S)-PPT］ via two routes, and their formation mechanism has been speculated. Route 1: Compounds 3 and 4 were obtained from 20(S)-PPT by oxidation with m-CPBA at the yield of 44. 1% and 28. 6%, respectively. Route 2: Compounds 3 and 4 were prepared from 20(S)-PPT by acetylation, oxidation and saponification at the yield of 16. 4% and 16. 2%, respectively. The formation mechanism of compounds 3 and 4 is speculated as below: 1)The chemical environments of both sides of C24(25)double bond in 20(S)-PPT are different due to the existence of intramolecular hydrogen bond, which led to the different oxidation ratio of the two sides, and the different yields of compounds 3 and 4 . 2)There is not intramolecular hydrogen bond in acetylated 20(S)-PPT, and the chemical environments of both sides of C24(25)double bond are similar, which resulted in almost equal yields of compounds 3 and 4 synthesized through oxidation with m-CPBA, intramolecular S_N2 and saponification.
- ocotillol,
- epimer,
- synthesis,
- formation mechanism

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