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Synthesis 2017; 49(22): 4899-4916
DOI: 10.1055/s-0036-1588577
DOI: 10.1055/s-0036-1588577
review
Synthetic Approaches to 2,6-trans-Tetrahydropyrans
This research was financially supported by the Research Grant Council of Hong Kong (GRF 605113, GRF 16305314, and GRF 16311716), HKUST (Start-up R9309) and the National Natural Science Foundation of China (No. 21472160)
Further Information
Publication History
Received: 15 June 2017
Accepted after revision: 12 July 2017
Publication Date:
28 September 2017 (online)
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 SN2 Substitution and Epoxide Opening (Strategy B)
7 Miscellaneous Methods
8 Conclusion and Outlook
-
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