Download PDF
Synlett 1993; 1993(12): 901-905
DOI: 10.1055/s-1993-22645
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.

Oxidative Degradation of γ-Butyrolactons into 1,3-Diols via a Criegee Rearrangement of Peroxosulfonates. An Enantioselective Synthesis of Compactin Lactone and its Diastereomer

Markus Menges* , Reinhard Brückner
  • *Institut für Organische Chemie, Georg-August-Universität, Tammannstr. 2, D-37077 Göttingen, Germany
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The sterically homogenous α,γ-disubstituted γ-butyrolactones trans- and cis-10 were degraded stereoselectively to the 1,3-diols anti-16 and syn-16, respectively. The key step of these transformations were Criegee rearrangements of peroxosulfonates derived from hemiketal peroxides. Syn-16 was transformed into the δ-valerolactone 19 which is a synthon for the compactin lactone. Anti-16 was similarly converted into the diastereomeric valerolactone iso-19.

      >