Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Abstract Being different from 2,6- cis -tetrahydropyrans (2,6- cis -THPs), the corresponding 2,6- trans -THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6- trans -THP subunit has led...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2017-11, Vol.49 (22), p.4899-4916
Main Authors: Zhang, Zhihong, Tong, Rongbiao
Format: Article
Language:English
Subjects:
review
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Summary:Abstract Being different from 2,6- cis -tetrahydropyrans (2,6- cis -THPs), the corresponding 2,6- trans -THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6- trans -THP subunit has led to the development of many efficient synthetic approaches to access 2,6- trans -THPs. This review summarizes various synthetic methods reported for this structural motif and/or related applications in the total synthesis of natural products. 1 Introduction 2 Nucleophilic Addition to an Oxocarbenium Ion (Strategy A) 3 Intramolecular Oxa-Michael Addition (Strategy B) 4 Intermolecular Michael Addition to Dihydropyranones (Strategy A) 5 The Heck–Matsuda (Strategy A) Reaction and Oxa-Heck Cyclization (Strategy B) 6 Intramolecular S N 2 Substitution and Epoxide Opening (Strategy B) 7 Miscellaneous Methods 8 Conclusion and Outlook
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588577