ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The spiro[cyclohexane-1,2′-[2H]indene] derivatives 15a,b with molecular dimensions and nucleophilic functional groups similar to known steroid 5α-reductase inhibitors (e.g. 2) were synthesized. The spiro[cyclohexane-1,2′-[2H]indene]-1′(3′H),4-dione (5) was synthesized from 5-methoxyindan-l-one ( = 2,3-dihydro-5-methoxy-1H-inden-1-one). A Grignard reaction and a dehydration step led to the cyclohexene (±)-7 which, upon a stereoselective hydrogenation catalyzed by Raney-Ni under mild conditions, gave 8a as a pure epimer. Further hydrogenation and hydrogenolysis of 8a over Pd/C at room temperature reduced the keto group to give pure 9a. Finally, the 5′-substituted derivatives 12a, 14a, and 15a were generated by deprotection and Heck-type reaction.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780407
