Citation: Zhi Yong Tang Chen Xi Zhang, Li Jing Fang, Yu Lin Li. The first facile total synthesis of natural (3R,4R,6S)-3,4-epoxybisabola-7(14),10-dien-2-one[J]. Chinese Chemical Letters, ;2009, 20(9): 1017-1018. doi: 10.1016/j.cclet.2009.03.010 shu

The first facile total synthesis of natural (3R,4R,6S)-3,4-epoxybisabola-7(14),10-dien-2-one

State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Received Date: 24 December 2008

Fund Project: This work was financially supported by the National Science Foundation of China (No.20272021).

3,4-Epoxybisabola-7(14),10-dien-2-one, a natural sesquiterpoind, was first synthesized from (-)-carvone through 7 steps, in an overall yield of 35.9%. The key step was the allylation and then a substrate-directable epoxidation was committed successfully.Mycobacterium tuberculosis FabH, an essential enzyme in mycolic acids biosynthetic pathway, is an attractive target for novel anti-tuberculosis agents. Structure-based design, synthesis of novel inhibitors of mtFabH was reported in this paper. A novel scaffold structure was designed, and 12 candidate compounds that displayed favorable binding with the active site were identified and synthesized.
- Alkylation,
- Epoxidation,
- Synthesis
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