ISSN:
0947-3440
Keywords:
Cyclic vicinal tetraketones
;
Rubottom reaction
;
Medium-sized rings
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 mCPBA 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199509230