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Synlett 1996; 1996(2): 129-130
DOI: 10.1055/s-1996-5353
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Expedient Enantiocontrolled Synthesis of a Tetracyclic Lactone Structurally Related to the Kaurane Diterpenoids

Leo A. Paquette* , Hon-Chung Tsui
  • *Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210, USA, FAX: (614) 292-1685; Internet: lpaquett@magnus.acs.ohio-state.edu
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Publication Date:
31 December 2000 (online)

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Coupling of enantiopure samples of bicyclic ketone 1 and vinyl bromide 2 afforded predominantly 4, anionic oxy-Cope rearrangement of which gave rise efficiently to 5. Following Mitsunobu inversion of the allylic hydroxyl, sequential ester Claisen rearrangement, saponification, and iodolactonization-elimination afforded 9, whose ketalization to provide 10 was not sterically impeded.

dihydrobenzene diol - oxy-Cope rearrangement - cerium-promoted coupling - chirality transfer - bicyclo[2.2.2]octenones