Download PDF
Synlett 1996; 1996(2): 129-130
DOI: 10.1055/s-1996-5353
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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