Synthesis 2015; 47(18): 2756-2766
DOI: 10.1055/s-0034-1380221
special topic
© Georg Thieme Verlag Stuttgart · New York

Hexahydro-1H-Isoindolinone-Like Scaffolds from Electronically Deactivated and Sterically Hindered Dienes: Synthesis in the Context­ of Muironolide A

Christopher A. Olson
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA   Email: tmitche@ilstu.edu
,
Courtnay E. Shaner
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA   Email: tmitche@ilstu.edu
,
Sydney C. Roche
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA   Email: tmitche@ilstu.edu
,
Gregory M. Ferrence
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA   Email: tmitche@ilstu.edu
,
T. Andrew Mitchell*
Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA   Email: tmitche@ilstu.edu
› Author Affiliations
Further Information

Publication History

Received: 30 April 2015

Accepted after revision: 05 June 2015

Publication Date:
05 August 2015 (eFirst)

Abstract

Initial synthetic efforts toward muironolide A based upon an intramolecular Diels–Alder strategy were hampered by a conjugate reduction rather than the desired half-reduction. An intermolecular Diels–Alder strategy was initiated that utilized electronically deactivated and sterically hindered dienes. The [4+2] cycloadditions were successful, but only with highly reactive dipolarophiles such as N-phenylmaleimide and 4-phenyl-1,2,4-triazoline-3,5-dione thus establishing the scope of these dienes. Although limited, installation of the α,β-unsaturated lactam embedded in the hexahydro-1H-isoindolinone is noteworthy.

Supporting Information

 
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