Facile Total Synthesis of 3-Oxo-11,12,13-trihydroxyeudesm-4-ene

Chem. J. Chinese Universities

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Facile Total Synthesis of 3-Oxo-11,12,13-trihydroxyeudesm-4-ene

GUAN Yu-Kun^1,2*, FANG Li-Jing², TANG Zhi-Yong², LI Yu-Lin²

1. School of Pharmacy, Yantai University, Yantai 264005, China;
2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Received:2006-10-17 Revised:1900-01-01 Online:2007-07-10 Published:2007-07-10
Contact: GUAN Yu-Kun

Abstract

Abstract:

3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity. For the purpose of pharmacological activity research on natural product 1 and its derivatives, a facile total synthesis of compound 1 starting from (+)-dihydrocarvone(2) was completed in an overall yield of 24%. The structures of all intermediates and product 1 were confirmed via ¹H NMR, ¹³C NMR, MS and IR techniques. The NMR data of compound 1 are in agreement with those of natural products.

Key words: Eudesmane, 3-Oxo-11,12,13-trihydroxyeudesm-4-ene, Total synthesis, Sesquiterpene

CLC Number:

O621.3

TrendMD:

GUAN Yu-Kun^1,2*, FANG Li-Jing², TANG Zhi-Yong², LI Yu-Lin². Facile Total Synthesis of 3-Oxo-11,12,13-trihydroxyeudesm-4-ene[J]. Chem. J. Chinese Universities, doi: .

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Facile Total Synthesis of 3-Oxo-11,12,13-trihydroxyeudesm-4-ene

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