Studies on Synthesis of the C-1 to C-18 Fragment of Pamamycins 607 and 621A
作者： Guobao Ren , Yikang Wu
关键词: Stereochemistry 、 Stereocenter 、 Fragment (computer graphics) 、 Substrate (chemistry) 、 Aldol reaction 、 Malic acid 、 Ketone 、 Chemistry 、 Enantioselective synthesis 、 Alcohol 、 General chemistry
摘要: Some efforts directed towards synthesis of the C-1 to C-18 fragment natural antibiotic pamamycins 607 and 621A are disclosed. The nine stereogenic centers in were installed using a chiral auxiliary-induced asymmetric aldol reaction, building block derived from malic acid, or substrate chirality-induced reduction ketone carbonyl group.
sci-hub.se 参考文章(26)
Benjamin H. Fraser, Roger J. Mulder, Patrick Perlmutter, The total synthesis of pamamycin-607. Part 2: Synthesis of the C6–C18 domain Tetrahedron. ,vol. 62, pp. 2857- 2867 ,(2006) , 10.1016/J.TET.2006.01.005
Ikuko Kozone, Makoto Hashimoto, Udo Gräfe, Hiroshi Kawaide, Hiroshi Abe, Masahiro Natsume, Structure-activity Relationship of Pamamycins: Effect of Side Chain Length on Aerial Mycelium-inducing Activity The Journal of Antibiotics. ,vol. 61, pp. 98- 102 ,(2008) , 10.1038/JA.2008.118
James C. Anderson, Benjamin P. McDermott, Edward J. Griffin, Asymmetric Epoxide Cyclisation Route to the F-pyran Fragment of the Altohyrtins and Key Aldol Studies Tetrahedron. ,vol. 56, pp. 8747- 8767 ,(2000) , 10.1016/S0040-4020(00)00804-8
Sung Ho Kang, Joon Won Jeong, Yu Sang Hwang, Sung Bae Lee, Total Synthesis of (+)-Pamamycin-607 Angewandte Chemie International Edition. ,vol. 41, pp. 1392- 1395 ,(2002) , 10.1002/1521-3773(20020415)41:8<1392::AID-ANIE1392>3.0.CO;2-G
Michael T. Crimmins, Bryan W. King, Elie A. Tabet, Asymmetric Aldol Additions with Titanium Enolates of Acyloxazolidinethiones: Dependence of Selectivity on Amine Base and Lewis Acid Stoichiometry Journal of the American Chemical Society. ,vol. 119, pp. 7883- 7884 ,(1997) , 10.1021/JA9716721
Ayako Miura, Shin-ya Takigawa, Yukito Furuya, Yusuke Yokoo, Shigefumi Kuwahara, Hiromasa Kiyota, Synthesis of the L‐Acid (C1–C18) Fragment of Pamamycin‐593 and De‐N‐methylpamamycin‐579 European Journal of Organic Chemistry. ,vol. 2008, pp. 4955- 4962 ,(2008) , 10.1002/EJOC.200800600
Yikang Wu, Ya-Ping Sun, Synthesis of nonactin and the proposed structure of trilactone. Organic Letters. ,vol. 8, pp. 2831- 2834 ,(2006) , 10.1021/OL0609661
Steve Lanners, Hassan Norouzi-Arasi, Naima Khiri, Gilles Hanquet, Solvent-and structure-dependent regioselectivity in the boron-mediated aldol reaction of 2 -(1,3 -Dioxolan -2 -yl )ethyl ethyl ketones European Journal of Organic Chemistry. ,vol. 2007, pp. 4065- 4075 ,(2007) , 10.1002/EJOC.200700320
Jeong, Eun Joo Kang, Lee Taek Sung, Sung Kil Hong, Eun Lee, Stereoselective Synthesis of Pamamycin-607 Journal of the American Chemical Society. ,vol. 124, pp. 14655- 14662 ,(2002) , 10.1021/JA0279646
Michael T. Crimmins, Kleem Chaudhary, Titanium Enolates of Thiazolidinethione Chiral Auxiliaries: Versatile Tools for Asymmetric Aldol Additions Organic Letters. ,vol. 2, pp. 775- 777 ,(2000) , 10.1021/OL9913901