Tackling the Challenge of the Total Synthesis of Periploside A

Xiaheng Zhang; Biao Yu

doi:10.1055/s-0037-1610152

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(13): 1683-1692
DOI: 10.1055/s-0037-1610152

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Tackling the Challenge of the Total Synthesis of Periploside A

Autoren

Xiaheng Zhang

State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, P. R. of China eMail: byu@sioc.ac.cn
Biao Yu*

State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, P. R. of China eMail: byu@sioc.ac.cn

Abstract

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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

Key words

orthoester - formacetal - deoxysaccharides - dioxocarbenium - conformation - pregnane glycosides - glycosylation

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