Download PDF
Synlett 1996; 1996(4): 366-368
DOI: 10.1055/s-1996-5434
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.

Pd-Catalyzed Alkylation of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranose

Masakatsu Matsumoto* , Hiromi Ishikawa, Takayuki Ozawa
  • *Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-12, Japan
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The palladium(0)-catalyzed substitution of 1,6-anhydro-2-chloro-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranose (2) with active methylene compounds (4a-c) proceeds smoothly to give predominantly 4-substituted products (5) together with 2-isomers (6). The reaction is applied to the synthesis of a key intermediate for thromboxanes and quinuclidinol.

palladium catalyst - levoglucosenone - nucleophilic substitution - alkylation - active methylene compounds - thromboxanes

      >