Journal of Organic Chemistry p. 2380 - 2390 (1990)
Update date:2022-08-02
Topics:
Piers, Edward
Gavai, Ashvinikumar V.
Transmetalation of (Z)-5-chloro-3-trimethylstannyl-2-pentene (8) with MeLi in tetrahydrofuran (THF) at -78 deg C provides the novel bifunctional reagent (E)-5-chloro-3-lithio-2-pentene (11), which can be transformed readily into the Grignard reagent (12).Copper(I)-catalyzed conjugate addition of (12) to cyclic α,β-unsatured ketones (e.g., 23-29), followed by intramolecular alkylation of the resultant chloro ketones (e.g., 30-36), affords the corresponding (Z)-ethylidenecyclopentane annulation products (e.g., 37-43).This new annulation method played a key role intotal syntheses of the sesquiterpenoids (+/-)-anhydrooplopanone (51), (+/-)-oplopanone (50), and (+/-)-8-epi-oplopanone (70).
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