Convenient Synthesis of Angular Triquinane from 4-Alkenylfulvene via Thermal Cycloaddition Followed by Skeletal Rearrangement of the Resulting [4 + 2] Adduct

Cyclopentane derivatives Q 0030 Convenient Synthesis of Angular Triquinane from 4-Alkenylfulvene via Thermal Cycloaddition Followed by Skeletal Rearrangement of the Resulting [4 + 2] Adduct. -Alkenylfulvalene (III), prepared by the annulation of phosphorane (II) with dione (I), undergoes intramolecular cycloaddition in a highly regio-and stereoselective manner. Hydrolysis of the enol-ether group gives adduct (IV). Subsequent treatment of (IV) with LHMDS/tBuOK affords the target triquinane derivative (V). -(INAGAKI, S.; IMURA, K.; MORITA, T.; YOSHIMI, Y.; HATANAKA*, M.; KAWANO, T.; Chem. Lett. 37 (2008) 4, 454-455; Dep. Appl. Chem. Biotechnol., Fac. Eng., Fukui Univ., Bunkyo, Fukui 910, Japan; Eng.) -M. Paetzel 34-063

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A new approach toward the bicyclo[3.2.1]octenes via a carbocation-based cyclization from unusually functionalized seven-membered ring precursors

Zhang

Cheng

et al. 2015

Tetrahedron

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Convenient Synthesis of Angular Triquinane from 4-Alkenylfulvene via Thermal Cycloaddition Followed by Skeletal Rearrangement of the Resulting [4 + 2] Adduct

Cited by 5 publications

References 19 publications

Molecular Rearrangements: Part 2. Other Reactions

Molecular Rearrangements: Part 2. Other Reactions

ChemInform Abstract: Convenient Synthesis of Angular Triquinane from 4‐Alkenylfulvene via Thermal Cycloaddition Followed by Skeletal Rearrangement of the Resulting [4 + 2] Adduct.

A new approach toward the bicyclo[3.2.1]octenes via a carbocation-based cyclization from unusually functionalized seven-membered ring precursors

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