Chemistry of xanthorrhizol: synthesis of several bisabolane sesquiterpenoids from xanthorrhizol

Abstract—()-Xanthorrhizol (1) isolated from the rhizomes of Curcuma xanthorrhiza has been transformed to several bisabolanetype sesquiterpenoids, in a stereoselective manner. 10R- and 10S-10,11-dihydro-10,11-dihydroxyxanthorrhizols (2, 3), ()-curcuquinone (4), ()-curcuhydroquinone (5), helibisab...

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Bibliographic Details
Main Authors: Sirat, Hasnah, Ngai, Mun Hong, Jauri, Mohd. Haffiz
Format: Article
Language:English
Published: Elsevier 2007
Subjects:
Online Access:http://eprints.utm.my/2489/
http://eprints.utm.my/2489/1/HasnahMSirat2007_Chemistryofxanthorrhizolsynthesis.pdf
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Summary:Abstract—()-Xanthorrhizol (1) isolated from the rhizomes of Curcuma xanthorrhiza has been transformed to several bisabolanetype sesquiterpenoids, in a stereoselective manner. 10R- and 10S-10,11-dihydro-10,11-dihydroxyxanthorrhizols (2, 3), ()-curcuquinone (4), ()-curcuhydroquinone (5), helibisabonol A (7) and allylic alcohol 8 have been prepared from xanthorrhizol in optically active forms. All the routes involved a Sharpless AD to introduce the stereogenic centre at C-10. 2006 Elsevier Ltd. All rights reserved.