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Total synthesis of(+)-lentiginosine via a key Au catalysis

Total synthesis of(+)-lentiginosine via a key Au catalysis
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摘要 Total syntheses of(+)-lentiginosine and its 8a-epimer using a gold-catalyzed oxidative cyclization as the key step were realized.The gold chemistry,reported previously in a 4+2 synthesis of piperidin-4-ones,tolerates functionalized structures and is compatible with several protecting strategies albeit with low diastereose lectivities. Total syntheses of(+)-lentiginosine and its 8a-epimer using a gold-catalyzed oxidative cyclization as the key step were realized.The gold chemistry,reported previously in a 4+2 synthesis of piperidin-4-ones,tolerates functionalized structures and is compatible with several protecting strategies albeit with low diastereose lectivities.
作者 CUI Li & ZHANG LiMing Department of Chemistry & Biochemistry,University of California,Santa Barbara,CA 93106,USA
出处 《Science China Chemistry》 SCIE EI CAS 2010年第1期113-118,共6页 中国科学（化学英文版）
基金 Supported by the National Science Foundation,USA (CAREER CHE-0969157) and UCSB
关键词 GOLD TOTAL synthesis CYCLIZATION OXIDATION ALKALOID gold total synthesis cyclization oxidation alkaloid
分类号 O643.3 [理学—物理化学]
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参考文献34

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  • 3Yoda H,Kitayama H,Katagiri T,Takabe K.Synthesis of natural len- tiginosine employing a cyclic imide with C-2-symmetry derived from L-tartaric acid. Tetrahedron Asymmetry . 1993
  • 4Gurjar MK,Ghosh L,Syamala M,Jayasree V.Stereoselective syn- thesis of (+)-leniginosine and (-)-lentiginosine. Tetrahedron Letters . 1994
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  • 8Chen M-J,Tsai Y-M.Intramolecular Alpha-acylamino radical cycli- zations with acylsilanes in the preparation of polyhydroxylated alka- loids: (+)-lentiginosine, (+)-1,8a-di-epi-lentiginosine, and (+)-1,2-di- epi-swainsonine. Tetrahedron Letters . 2007
  • 9Alam MA,Vankar YD.Total synthesis of (+)-lentiginosine from D-glucose. Tetrahedron Letters . 2008
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Science China Chemistry
2010年 第1期

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