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Synthesis 2015; 47(18): 2756-2766
DOI: 10.1055/s-0034-1380221
DOI: 10.1055/s-0034-1380221
special topic
Hexahydro-1H-Isoindolinone-Like Scaffolds from Electronically Deactivated and Sterically Hindered Dienes: Synthesis in the Context of Muironolide A
Further Information
Publication History
Received: 30 April 2015
Accepted after revision: 05 June 2015
Publication Date:
05 August 2015 (online)
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
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380221.
- Supporting Information
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