A concise and efficient total synthesis of alkaloid narceine imide is disclosed. The key steps are based upon the sequential construction of the isoindolinone template followed by metalation and coupling with an isoquinolinium salt. Subsequent E1cb elimination enables the creation of the arylmethylene unit with the concomitant formation of the dimethylaminoethyl chain and ultimate deprotection completes the synthesis of the natural product.
1 December 2002 in Bioorganic & Medicinal Chemistry Letters
The first total synthesis of the phytotoxins cichorine and zinnimidine is described. The synthetic tactics involve the sequential connection of the dense and diverse functionalities on the aromatic nucleus followed by a Parham cyclization process, giving rise to the lactam unit embedded in the title compound framework.
A variety of diversely substituted isoindolin-1-ones have been prepared by alkaline cleavage of the C-P pond in the corresponding phosphorylated lactams obtained by base-induced arynemediated cyclization of o-halogeno-N-(phosphinylmethyl)benzamide derivatives.