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Synthesis of 5,5,10,10-tetramethyl-1-oxacyclotridecane-6,7,8,9-tetrone – on the mechanism of the Rubottom reaction

✍ Scribed by Gleiter, Rolf ;Staib, Michael ;Ackermann, Uwe

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
785 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The synthesis of 5,5,10,10‐tetramethyl‐1‐oxacyclotridecan‐6,7,8,9‐tetrone (12) was achieved via a multistep procedure involving an oxidation known as the Rubottom reaction. The key intermediates were the dialdehyde (25), the diacid (33), the cyclic diketone (39) and the bis(silyl enol ether) (42). The oxidation of 42 with __m__CPBA yielded two diastereomers, the syn and anti bis(α‐hydroxy ketones) (44, 45) the ratio of which depends strongly on the solvent used. This result combined with the isolation of the diepoxide (43) gives an insight into the stereochemistry of the Rubottom reaction.

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