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Strategies and Tactics in Organic Synthesis
Jenny B. WernessWei ZhangWeiping Tang
其他書名
Chapter 10. Stereoselective Addition of Halogen to Conjugated Enynes and Its Application in the Total Synthesis of (−)-Kumausallene
出版Elsevier Inc. Chapters, 2013-07-29
主題Science / Chemistry / Organic
ISBN01280561349780128056134
URLhttp://books.google.com.hk/books?id=njdzDAAAQBAJ&hl=&source=gbs_api
EBookSAMPLE
註釋Addition of halogen and nucleophiles to conjugated 1,3-enynes in a 1,4-fashion produces a chiral allene and a stereogenic center. The diastereo- and enantioselectivity of this process are discussed in detail. The 1,4-bromoetherification of 1,3-enynes can be applied to the synthesis of various bromoallene-containing natural products. Our diastereo- and enantioselective total synthesis of kumausallene is described in this chapter. The synthesis features a cascade reaction involving palladium-catalyzed desymmetrization and a DMF-mediated diastereoselective 1,4-bromoetherification reaction.