Download PDF
Synlett 1996; 1996(8): 785-786
DOI: 10.1055/s-1996-5532
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.

Stereoselective Synthesis of Tropane Alkaloids: Physoperuvine and Dihydroxytropanes

Marek Majewski* , Ryszard Lazny
  • *Department of Chemistry, University of Saskatchewan, 110 Science Pl., Saskatoon, SK S7N 5C9, Canada, Fax: 306 966 4730; E-mail: Majewski@sask.usask.ca
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Deprotonation of tropinone (1) with a chiral lithium amide produces the corresponding Li-enolate in over 95% ee. The enolate undergoes a ring opening reaction upon treatment with chloroformates. The resulting substituted cycloheptenone 3 can be used in synthesis of physoperuvine (via the Wharton reaction) and also as a building block for synthesis of dihydroxytropanes: tropane alkaloids having a hydroxy group at C-6 or C-7 and an acyloxy group at C-3.

chiral lithium amides - deprotonation - tropane alkaloids

      >