Oxidative Degradation of γ-Butyrolactons into 1,3-Diols via a Criegee Rearrangement of Peroxosulfonates. An Enantioselective Synthesis of Compactin Lactone and its Diastereomer
- 1 January 1993
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1993 (12) , 901-905
- https://doi.org/10.1055/s-1993-22645
Abstract
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.Keywords
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