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

Autor:	Christopher A. Olson, T. Andrew Mitchell, Gregory M. Ferrence, Sydney C. Roche, Courtnay E. Shaner
Rok vydání:	2015
Předmět:	Steric effects chemistry.chemical_compound chemistry Intramolecular force Organic Chemistry Lactam Organic chemistry Total synthesis Context (language use) Catalysis Cycloaddition Diels–Alder reaction
Zdroj:	Synthesis. 47:2756-2766
ISSN:	1437-210X 0039-7881
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1fd23d19846c332d07832d3ba863721b https://doi.org/10.1055/s-0034-1380221 Zobrazit plný text záznamu