Molecules 2011, 16(5), 4165-4171; doi:10.3390/molecules16054165
Communication

A Regioselective Synthesis of E-Guggulsterone

Jungyeob Ham 1 email, Jungwook Chin 2,3,* email and Heonjoong Kang 2,3,* email
1 Korea Institute of Science and Technology, 290 Daejeon-dong, Gangneung 210-340, Korea 2 Center for Marine Natural Products and Drug Discovery, School of Earth and Environmental Sciences, Seoul National University, NS-80, Seoul 151-747, Korea 3 Research Institute of Oceanography, Seoul National University, NS-80, Seoul 151-741, Korea
* Authors to whom correspondence should be addressed.
Received: 18 April 2011; in revised form: 17 May 2011 / Accepted: 18 May 2011 / Published: 20 May 2011
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Abstract: We have successfully prepared E-guggulsterone from 16,17-epoxy-pregnenolone in 84% yield over two steps via a hydrazine reduction and Oppenhauer oxidation. Additionally, isomerization was induced by heat, light (hn) and acid catalysis to convert E- guggulsterone into the corresponding Z isomer.
Keywords: guggulsterone; inflammatory bowel diseases; regioselective synthesis; oppenhauer oxidation

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Cite This Article

MDPI and ACS Style

Ham, J.; Chin, J.; Kang, H. A Regioselective Synthesis of E-Guggulsterone. Molecules 2011, 16, 4165-4171.

AMA Style

Ham J, Chin J, Kang H. A Regioselective Synthesis of E-Guggulsterone. Molecules. 2011; 16(5):4165-4171.

Chicago/Turabian Style

Ham, Jungyeob; Chin, Jungwook; Kang, Heonjoong. 2011. "A Regioselective Synthesis of E-Guggulsterone." Molecules 16, no. 5: 4165-4171.

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