Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Zhihong Zhang; Rongbiao Tong

doi:10.1055/s-0036-1588577

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(22): 4899-4916
DOI: 10.1055/s-0036-1588577

review

Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Autoren

Zhihong Zhang

^aDepartment of Chemistry, The Hong Kong University of Science and Technology (HKUST), Clearwater Bay, Kowloon, Hong Kong, P. R. of China
Rongbiao Tong *

^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

Abstract

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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

Volltext

Referenzen

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