An enantioselective approach to (−)-platencin via catalytic asymmetric intramolecular cyclopropanation
作者： Sho Hirai , Masahisa Nakada
DOI: 10.1016/J.TETLET.2010.07.088
关键词: Organic chemistry 、 Stereochemistry 、 Catalysis 、 Total synthesis 、 Chemistry 、 Enantioselective synthesis 、 Cyclopropanation 、 Intramolecular force
摘要: Abstract This Letter describes an enantioselective approach to (−)-platencin. A uniquely functionalized chiral intermediate, which was prepared via the highly catalytic asymmetric intramolecular cyclopropanation (CAIMCP) that we have developed, successfully transformed Nicolaou’s intermediate in his total synthesis of
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sci-hub.se 参考文章(65)
Hong C. Shen, Fa-Xiang Ding, Sheo B. Singh, Gopalakrishnan Parthasarathy, Stephen M. Soisson, Sookhee N. Ha, Xun Chen, Srinivas Kodali, Jun Wang, Karen Dorso, James R. Tata, Milton L. Hammond, Malcolm MacCoss, Steven L. Colletti, Synthesis and biological evaluation of platensimycin analogs Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 1623- 1627 ,(2009) , 10.1016/J.BMCL.2009.02.006
Jun Wang, Srinivas Kodali, Sang Ho Lee, Andrew Galgoci, Ronald Painter, Karen Dorso, Fred Racine, Mary Motyl, Lorraine Hernandez, Elizabeth Tinney, Steven L. Colletti, Kithsiri Herath, Richard Cummings, Oscar Salazar, Ignacio González, Angela Basilio, Francisca Vicente, Olga Genilloud, Fernando Pelaez, Hiranthi Jayasuriya, Katherine Young, Doris F. Cully, Sheo B. Singh, Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 104, pp. 7612- 7616 ,(2007) , 10.1073/PNAS.0700746104
Krishna P. Kaliappan, Velayutham Ravikumar, An expedient enantioselective strategy for the oxatetracyclic core of platensimycin. Organic Letters. ,vol. 9, pp. 2417- 2419 ,(2007) , 10.1021/OL070848T
Hideaki Watanabe, Masashi Takano, Akinori Umino, Toshiya Ito, Hiroyuki Ishikawa, Masahisa Nakada, Enantioselective total synthesis of (-)-erinacine B. Organic Letters. ,vol. 9, pp. 359- 362 ,(2007) , 10.1021/OL0628816
Chaowei Zhang, John Ondeyka, Ziqiang Guan, Lisa Dietrich, Bruce Burgess, Jun Wang, Sheo B Singh, Isolation, structure and biological activities of platensimycin B4 from Streptomyces platensis The Journal of Antibiotics. ,vol. 62, pp. 699- 702 ,(2009) , 10.1038/JA.2009.106
Konrad Tiefenbacher, Johann Mulzer, Short Formal Synthesis of (−)‐Platencin Angewandte Chemie. ,vol. 47, pp. 6199- 6200 ,(2008) , 10.1002/ANIE.200801441
Masahiro Honma, Masahisa Nakada, Enantioselective total synthesis of (+)-digitoxigenin Tetrahedron Letters. ,vol. 48, pp. 1541- 1544 ,(2007) , 10.1016/J.TETLET.2007.01.024
Chaowei Zhang, John Ondeyka, Deborah L. Zink, Bruce Burgess, Jun Wang, Sheo B. Singh, Isolation, structure and fatty acid synthesis inhibitory activities of platensimycin B1-B3 from Streptomyces platensis. Chemical Communications. pp. 5034- 5036 ,(2008) , 10.1039/B810113B
Masahito Abe, Masahisa Nakada, New construction of the bicyclo[3.3.1]nonane system via Lewis acid promoted regioselective ring-opening reaction of the tricyclo[4.4.0.05,7]dec-2-ene derivative Tetrahedron Letters. ,vol. 47, pp. 6347- 6351 ,(2006) , 10.1016/J.TETLET.2006.07.010
K. C. Nicolaou, Antonia F. Stepan, Troy Lister, Ang Li, Ana Montero, G. Scott Tria, Craig I. Turner, Yefeng Tang, Jianhua Wang, Ross M. Denton, David J. Edmonds, Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity Journal of the American Chemical Society. ,vol. 130, pp. 13110- 13119 ,(2008) , 10.1021/JA8044376