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 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_N2 Substitution and Epoxide Opening (Strategy B)

7 Miscellaneous Methods

8 Conclusion and Outlook

Key words

2,6-trans-tetrahydropyran - oxocarbenium ions - (oxa-)Michael addition - Heck reaction - epoxide opening

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