1474103-48-4Relevant academic research and scientific papers
Synthetic efforts toward the isoindolinone core of muironolide A
Shaner, Courtnay E.,Ferrence, Gregory M.,Mitchell, T. Andrew
, p. 1861 - 1864 (2013)
Studies directed toward the isoindolinone core of muironolide A are described. An initial plan to implement an intramolecular Diels-Alder cycloaddition was thwarted by an undesired conjugate addition during the attempted preparation of the Diels-Alder substrate. A revised retrosynthetic analysis revealed a direct, albeit challenging, intermolecular Diels-Alder disconnection. Toward this end, a sterically hindered and electronically deactivated diene was utilized with N-phenylmaleimide to achieve a Diels-Alder cycloaddition. Georg Thieme Verlag Stuttgart · New York.
Hexahydro-1 H -Isoindolinone-Like Scaffolds from Electronically Deactivated and Sterically Hindered Dienes: Synthesis in the Context of Muironolide A
Olson, Christopher A.,Shaner, Courtnay E.,Roche, Sydney C.,Ferrence, Gregory M.,Mitchell, T. Andrew
, p. 2756 - 2766 (2015/09/15)
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.
