Synthesis
DOI: 10.1055/s-0036-1588577
review
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Zhihong Zhanga, Rongbiao Tong*a, b
  • aDepartment of Chemistry, The Hong Kong University of Science and Technology (HKUST), Clearwater Bay, Kowloon, Hong Kong, P. R. of China
  • bHKUST Shenzhen Research Institute, Shenzhen 518057, P. R. of China   rtong@ust.hk
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 (eFirst)

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