Stereoselective Synthesis of Tetrahydrofuran Lignans

Darunee Soorukram; Manat Pohmakotr; Chutima Kuhakarn; Vichai Reutrakul

doi:10.1055/s-0037-1610289

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4746-4764
DOI: 10.1055/s-0037-1610289

short review

Stereoselective Synthesis of Tetrahydrofuran Lignans

Darunee Soorukram*

Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand Email: darunee.soo@mahidol.ac.th

,

Manat Pohmakotr

,

Chutima Kuhakarn

,

Vichai Reutrakul

› Author Affiliations

Abstract

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Abstract

This short review aims to summarize the reports on stereoselective synthesis of naturally occurring tetrahydrofuran lignans published during the period of 2006 to 2018. The stereoselective construction of non-natural tetrahydrofuran frameworks is not included in this review.

1 Introduction

2 Stereoselective Synthesis of 2,5-Diaryltetrahydrofuran (CL5-a)

2.1 Synthesis of CL5-a via Friedel–Crafts Arylation or Nucleophilic Addition/Reduction of γ-Butyrolactones

2.2 Synthesis of CL5-a via Intramolecular Cyclization of 1,4-Diarylbutanediols

2.3 Synthesis of CL5-a via Diastereoselective Hydrogenation of Furan Derivatives

2.4 Synthesis of CL5-a via Cycloaddition Reaction of Substituted Cyclopropane Derivatives

3 Stereoselective Synthesis of 2-Aryl-4-benzyltetrahydrofuran (CL5-b)

4 Stereoselective Synthesis of 3,4-Dibenzyltetrahydrofuran (CL5-c)

5 Conclusions

Key words

lignans - furans - stereoselective synthesis - bioactive compounds - natural products

Full Text

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