Kasturi, Tirumalai R. ; Pragnacharyulu, Palle V. P. ; Reddy, Gouravaram M. ; Jayaram, Srirangam K. ; Singh, Sheo B. (1992) Oxidation of spiroketones with DDQ - synthesis of tropone derivatives and DDHQ diesters Tetrahedron, 48 (26). pp. 5481-5496. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)88302-2
Abstract
Oxidation of spiroketones 3a-f with DDQ in dry benzene gave tropone derivatives 4a-f and DDHQ esters 5a-f (cis-cis isomer 6a-f, trans-trans isomer 7a-f). While the aryl substituted spirokeone 17a gave a 2:1 mixture of 19a and the corresponding trans-trans isomer, the aryl substituted spiroketones 17b-d gave exclusively cis?-cis? isomers 19b-d. Heating acid chloride of acid 9c with DDHQ resulted in compounds 4a and 7a, thus confirming the structures assigned. Mechanism of formation of these compounds has been rationalised. A detailed study of 2D 1H-1H COSY, 1H-13C COSY, HMBC and 2D NOESY of compound 7d led to complete assignment of 1H and 13C NMR signals and its solution conformation.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 16070 |
| Deposited On: | 15 Nov 2010 14:16 |
| Last Modified: | 04 Jun 2011 04:25 |
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