Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans

Mei-Huey Lin; Yu-Chun Chen; Shih-Hao Chiu; Yun-Fan Chen; Tsung-Hsun Chuang

doi:10.3390/molecules21121713

Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans

Molecules. 2016 Dec 21;21(12):1713. doi: 10.3390/molecules21121713.

Authors

Mei-Huey Lin¹, Yu-Chun Chen², Shih-Hao Chiu³, Yun-Fan Chen⁴, Tsung-Hsun Chuang⁵

Affiliations

¹ Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan. mhlin@cc.ncue.edu.tw.
² Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan. stu01250008@gmail.com.
³ Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan. shihhao9239@yahoo.com.tw.
⁴ Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan. evons44@gmail.com.
⁵ Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan. th_chuang@hotmail.com.

Abstract

A new strategy for cyclopenta[b]furan synthesis mediated by hypervalent iodine(III) has been described. The approach employs diacetoxyiodobenzene-induced initial dehydrogenation to a putative trienone intermediate and triggered sequential cycloisomerization to form the cyclo-penta[b]furan targets.

Keywords: cycloisomerization; cyclopenta[b]furan; diacetoxyiodobenzene; domino oxidative cyclization; hypervalent iodine(III).

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Catalysis
Cyclization
Furans / chemical synthesis*
Iodine / chemistry*
Iodobenzenes / chemistry*
Isomerism
Molecular Structure
Oxidation-Reduction

Substances

Bridged Bicyclo Compounds, Heterocyclic
Furans
Iodobenzenes
Iodine