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Synlett 2018; 29(13): 1683-1692
DOI: 10.1055/s-0037-1610152
DOI: 10.1055/s-0037-1610152
account
Tackling the Challenge of the Total Synthesis of Periploside A
The financial support from the National Natural Science Foundation of China (21432012 & 21621002), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20020000), and the K. C. Wong Education Foundation is acknowledged.Further Information
Publication History
Received: 06 March 2018
Accepted after revision: 13 April 2018
Publication Date:
28 May 2018 (online)
Abstract
Periploside A is the prototypical congener of the pregnane glycosides occurring in the Chinese medicinal plant Periploca sepium, featuring a unique seven-membered formyl acetal bridged spiro-orthoester (FABO) sugar linkage and potent immunosuppressive activities. This account details our efforts on the stereoselective construction of the FABO motif that has led to a successful total synthesis of periploside A.
1 Introduction
2 Attempts at Construction of the FABO Motif
2.1 Intermolecular Condensation and Transacetalation
2.2 Intramolecular Hydrogen Atom Transfer (HAT) Reaction
3 Synthesis of the FABO Motif Bearing the Unnatural Anomeric Configuration
4 Synthesis of the FABO Motif Bearing the Natural Anomeric Configuration
4.1 Unsuccessful Attempts
4.2 Final Solution
5 Conclusion
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