Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

Xiao-Shui Peng; Ridge Michael P Ylagan; Yuk Ming Siu; Henry N C Wong

doi:10.1002/asia.201500288

Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

Chem Asian J. 2015 Oct;10(10):2070-83. doi: 10.1002/asia.201500288. Epub 2015 Jul 20.

Authors

Xiao-Shui Peng^{1

2}, Ridge Michael P Ylagan³, Yuk Ming Siu³, Henry N C Wong^{4

5}

Affiliations

¹ Department of Chemistry, State Key Laboratory of Synthetic Chemistry, Center of Novel Functional Molecules, and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China), Fax: (+852) 26035315. xspeng@cuhk.edu.hk.
² Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, and Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, The Chinese University of Hong Kong, No.10, Second Yuexing Road, Shenzhen, 518507, China. xspeng@cuhk.edu.hk.
³ Department of Chemistry, State Key Laboratory of Synthetic Chemistry, Center of Novel Functional Molecules, and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China), Fax: (+852) 26035315.
⁴ Department of Chemistry, State Key Laboratory of Synthetic Chemistry, Center of Novel Functional Molecules, and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China), Fax: (+852) 26035315. hncwong@cuhk.edu.hk.
⁵ Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, and Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, The Chinese University of Hong Kong, No.10, Second Yuexing Road, Shenzhen, 518507, China. hncwong@cuhk.edu.hk.

PMID: 26083458
DOI: 10.1002/asia.201500288

Abstract

The synthesis and application of [3.3.0]furofuranone species has received considerable attention from the scientific community. During the last twenty years, there has been a remarkable increase in publications focusing on their relevant method development as well as applications to natural product synthesis. This tutorial review discusses instructive examples to give a special emphasis on the development of new synthetic approaches and important applications to the total synthesis of natural products.

Keywords: domino reactions; furofuranones; natural products; synthesis; total synthesis.

Publication types

Research Support, Non-U.S. Gov't
Review

MeSH terms

Biological Products / chemistry*
Chemistry Techniques, Synthetic / methods
Heterocyclic Compounds / chemical synthesis*
Molecular Structure
Pharmaceutical Preparations / chemical synthesis
Pharmaceutical Preparations / chemistry

Substances

Biological Products
Heterocyclic Compounds
Pharmaceutical Preparations