The 1 -(wnitropropyl)-and 1 -(o-nitrobutyl)-6-hydroxytetralins 10 and 16, obtained by new sequences from 6-methoxytetralone, undergo stereospecific intramolecular coupling between phenolate and nitronate functions, to yield the tricyclospirodienones 11, 70%, and 17, 66%.There is considerable interest in the design and synthesis of new inhibitors for the cytochrome P-450 enzyme aromatase (P-450,,,,), which controls the conversion of androgens e.g. 1 to estrogens e.g. 2. Regulation of this activity is essential in the treatment of hormone-induced diseases, most notably estrogen-related mammary carcinoma. Much activity has focused on the synthesis of steroid relatives that can either bind to the iron centre, or react in a non-natural fashion, perhaps leading to suicide inhibition.'In our current work we aim to employ the effective steroid analogue system based on 2-aryldecalins, and to replace the (steroid) C-10 substituent with a functionalised bridged or fused ring.2 This would permit control over the stereochemistry of substituents in the proximity of the P-450 iron, allowing fixation of geometry in the sense suggested by computer graphics analysis. Our targets, thus, became those represented by the general structure 3. In view of the lack of suitable methodology for the synthesis of such compounds, we have developed new routes to 6,6,5-and 6,6,6-tricyclospirodienones from 6-methoxytetralone, one of which is reported here.
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