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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 10
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Original Articles

A NOVEL BASE-PROMOTED REARRANGEMENT OF EUDESMANOLIDE SESQUITERPENOID TO THE SALVIALANE SESQUITERPENE

Wu Jong Xia Department of Chemistry & National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China
,
Yong Qiang Tu Department of Chemistry & National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China
&
De Run Li Department of Chemistry & National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China
Pages 1613-1617 | Received 05 Jun 2000, Published online: 02 Aug 2010
 
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Abstract

An eudesmanolide sesquiterpene epoxide has been transformed to an α-hydroxy ketone with the salviane sesquiterpene skeleton through a novel carbon-carbon rearrangement promoted by excess of NaOMe in Et2O at room temperature which accomplished the first synthesis of the salviane kind of sesquiterpene skeleton. A possible reaction mechanism is also discussed.

ACKNOWLEDGMENTS

We are grateful for financial support from NNSFC(No. 29972019), FUKTME of China, the Young Teachers' Foundation of Ministry of Education and the Foundation of Ministry of Education (No. 99209).

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