Synthesis 2015; 47(18): 2713-2720
DOI: 10.1055/s-0034-1380429
special topic
© Georg Thieme Verlag Stuttgart · New York

A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols

Guo-Ying Luo
a  School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. China   Email: yutang@tju.edu.cn
,
Hao Wu
a  School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. China   Email: yutang@tju.edu.cn
,
Yu Tang*
a  School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. China   Email: yutang@tju.edu.cn
,
Hui Li
a  School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. China   Email: yutang@tju.edu.cn
b  Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53705, USA   Email: rhsung@wisc.edu
,
Hyun-Suk Yeom
b  Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53705, USA   Email: rhsung@wisc.edu
c  Korean Research Institute of Chemical Technology, Daejeon, South Korea
,
Ka Yang
a  School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. China   Email: yutang@tju.edu.cn
b  Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53705, USA   Email: rhsung@wisc.edu
,
Richard P. Hsung*
b  Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53705, USA   Email: rhsung@wisc.edu
› Author Affiliations
Further Information

Publication History

Received: 03 April 2015

Accepted after revision: 12 May 2015

Publication Date:
10 July 2015 (eFirst)

Abstract

Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation–oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.

Supporting Information

 
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