Total Synthesis of Sialic Acid by a Sequential Rhodium-Catalyzed Aziridination and Barbier Allylation of D-Glycal†
Dr. Rujee Lorpitthaya
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorDr. Sharad B. Suryawanshi
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorSiming Wang
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorKalyan Kumar Pasunooti
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorShuting Cai
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorDr. Jimei Ma
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dr. Xue-Wei Liu
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)Search for more papers by this authorDr. Rujee Lorpitthaya
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorDr. Sharad B. Suryawanshi
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorSiming Wang
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorKalyan Kumar Pasunooti
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorShuting Cai
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorDr. Jimei Ma
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dr. Xue-Wei Liu
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)Search for more papers by this authorWe thank Prof. Francois Mathey and Prof. Koichi Narasaka for fruitful discussions. We also thank Dr. Yong Xin Li for X-ray analyses and gratefully acknowledge Nanyang Technological University (NTU; RG 50/08) and the Ministry of Health (MOH; NMRC/H1N1R/001/2009) Singapore for financial support.
Graphical Abstract
Flexible Sequenz: Die Sialinsäure Neu5Ac wurde regio- und stereoselektiv aus einem Glycal über ein [1,2,3]-Oxathiazocan-2,2-dioxid-Intermediat synthetisiert (siehe Schema). Die Reaktionssequenz aus Rh-katalysierter Aziridinierung und Indium-vermittelter Barbier-Allylierung könnte eine flexible Route zu verschiedensten Sialinsäuren bieten, denn das Oxathiazocan war kompatibel mit einer Reihe von Nucleophilen.
Supporting Information
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