Download PDF
Synlett 2000; 2000(11): 1569-1572
DOI: 10.1055/s-2000-7936
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.

Demonstration of Stereospecificity in the β-Lactone-Initiated Spiroketal Synthesis

Ronald Zemribo* , Keith T. Mead
  • *Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA; Fax (6 62) 3 25-16 18; E-mail: kmead@ra.msstate.edu
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The one-pot spiroketalization of compound 1, terminating with equatorial substitution at the anomeric position, occurs with retention of configuration about the β-lactone stereogenic center and does not involve formation of a spiroketal oxocarbenium ion. A revised mechanism supported by semi-empirical calculations has been proposed for this reaction, consistent with these observations.

spiroketal synthesis - β-lactone - acetal cleavage

      >