ISSN:
0009-2940
Keywords:
Azulenones, cis-octa- and decahydro-
;
Stereoselective cyclization
;
Hydrogenation
;
Oxidation
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Medium and Large Rings, XXXV[1]. - Functionalized Hydroazulenones by Transannular Cyclizations of Dimethyl 10-Oxo-3,6-hexanooxepine-4,5-dicarboxylateTwo differently bridged hydroazulenones 2 and 3 are obtained in 69 and 61% yield, respectively, by treatment of the title compound 1 with sodium methoxide. The course of these intramolecular transannular cyclizations strongly depends on the amount of added base. 2 is hydrogenated to the ketones 9 and 10. Oxidative cleavage of the enol ether double bond of 3 and 10 leads to the octahydroazulene-1,6-dione 11 and to the decahydroazulene-3,8-dione 12, respectively.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931261219
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