Get access

Total Synthesis of Sialic Acid by a Sequential Rhodium-Catalyzed Aziridination and Barbier Allylation of D-Glycal

Authors

  • Dr. Rujee Lorpitthaya,

    1. 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 author
  • Dr. Sharad B. Suryawanshi,

    1. 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 author
  • Siming Wang,

    1. 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 author
  • Kalyan Kumar Pasunooti,

    1. 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 author
  • Shuting Cai,

    1. 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 author
  • Dr. Jimei Ma,

    1. 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 author
  • Prof. Dr. Xue-Wei Liu

    Corresponding author
    1. 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 author

  • We 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.

Abstract

original image

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.

Ancillary