Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione and First T...

Yong Rok Lee; Keon Yong Kang; Gun Joon Lee; Won Kyong Lee

doi:10.1055/s-2003-41023

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Synthesis 2003(13): 1977-1988
DOI: 10.1055/s-2003-41023

PAPER

Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione and First Total Synthesis of Millettocalyxins C and Pongamol Methyl Ether

Yong Rok Lee*, Keon Yong Kang, Gun Joon Lee, Won Kyong Lee
School of Chemical Engineering and Technology, College of Engineering Yeungnam University, Kyongsan 712-749, Korea
Fax: +82(53)8148790; e-Mail: yrlee@yu.ac.kr;

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Publication History

Received 2 April 2003
Publication Date:
19 August 2003 (online)

Abstract
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Abstract

Ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to vinyl sulfides afforded substituted dihydrofurans with sulfide groups in moderate yields. This new synthetic method has been applied to the synthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and furanoflavone natural products such as millettocalyxins C and pongol methyl ether.

Key words

furans - natural products - cycloadditions - oxidations - millettocalyxins C - pongol methyl ether

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