Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams

• Tetsuya Sengoku,
• Koki Makino,
• Ayumi Iijima,
• Toshiyasu Inuzuka and
• Hidemi Yoda

Beilstein J. Org. Chem. 2020, 16, 2769–2775, doi:10.3762/bjoc.16.227

• yields. On the other hand, methylene-lactone-fused spirolactams could be delivered from the allyl adducts in high yields through a sequential N-Boc protection/desulfinative lactonization. Keywords: bifurcated synthesis; electrophilic amide allylation; α-methylene-γ-butyrolactam; α-methylene-γ

• or N-Boc protection/desulfinative lactonization. The increase of diversity of structure accessible led to further understanding of the structure–cytotoxicity relationship of spirolactams on P388 cells. Syntheses of 3b–o via electrophilic amide allylation of γ-phenylthio lactams. Reactions were

• spirocyclic compounds through nucleophilic amide allylation, and (c) syntheses of spirocyclic compounds through electrophilic amide allylation. Syntheses of N-phenyl and N-alkyl-substituted spirolactams (two-step yields from 3). Screening of reaction conditions for electrophilic amide allylation. Supporting