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阿赫馬托維奇反應

維基百科,自由的百科全書

阿赫馬托維奇反應呋喃轉變為二氫吡喃環的過程,1971年由小奧斯曼·阿赫馬托維奇發現。[1] 最初方法是用糠醇甲醇中反應,先得到2,5-二甲氧基-二氫糠醇,它用稀硫酸發生重排便得到一個二氫吡喃衍生物。該衍生物與原甲酸甲酯三氟化硼反應上甲基保護基,接着用硼氫化鈉還原基,可得另一二氫吡喃衍生物,這個產物可用作許多單糖的合成中間體。

阿赫馬托維奇反應

這個反應用於天然產物desoxoprosophylline[2]核球殼菌素Pyrenophorin[3]包公藤甲素Bao Gong Teng A[4]全合成中。

最近也用於定向多樣性合成 [5] [6]

阿赫馬托維奇Burke 2006

以及 enantiomeric scaffolding 中。[7][8]

阿赫馬托維奇反應Coombs 2008

參見

參考資料

  1. ^ Synthesis of methyl 2,3-dideoxy--alk-2-enopyranosides from furan compounds : A general approach to the total synthesis of monosaccharides Tetrahedron, Volume 27, Issue 10, 1971, Pages 1973-1996 O. Achmatowicz, P. Bukowski, B. Szechner, Z. Zwierzchowska and A. Zamojski doi:10.1016/S0040-4020(01)98229-8
  2. ^ Asymmetric total synthesis of (+)-desoxoprosophylline Tetrahedron Letters, Volume 39, Issue 50, 10 December 1998, Pages 9227-9228 Cui-Fen Yang, Yi-Ming Xu, Li-Xin Liao and Wei-Shan Zhou doi:10.1016/S0040-4039(98)02129-7
  3. ^ Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)-Aspicilin, (+)-Patulolide A, and (-)-Pyrenophorin Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem.; (Article); 1998; 63(21); 7505-7515. doi:10.1021/jo980942a
  4. ^ Organometallic Enantiomeric Scaffolding: Organometallic Chirons. Total Synthesis of (-)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition Yongqiang Zhang and Lanny S. Liebeskind J. Am. Chem. Soc. 2006; 128(2) pp 465 - 472; (Article) doi:10.1021/ja055623x
  5. ^ A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. Am. Chem. Soc. 126 (43), 14095 -14104, 2004. doi:10.1021/ja0457415
  6. ^ 試劑為:NBSPPTS。另見固相合成
  7. ^ Practical, Scalable, High-Throughput Approaches to 3-Pyranyl and 3-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction Thomas C. Coombs, Maurice D. Lee, IV, Heilam Wong, Matthew Armstrong, Bo Cheng, Wenyong Chen, Alessandro F. Moretto, and Lanny S. Liebeskind J. Org. Chem. 73 (3), 882 -888, 2008. doi:10.1021/jo702006z
  8. ^ 過程為:氯甲酸苄酯為胺上Cbz保護基;mCPBA促進的阿赫馬托維奇反應;與的配位。Cp=環戊二烯基。