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