Octahydrophenanthrene Derivatives. Stereoselective Synthesis of the Isomeric 9,10-Dihydroxy-1,2,3,4,4a,9,10,10a-(trans-4a,10a)-Octahydrophenanthrenes
The four isomeric 9,10-dihydroxy-1,2,3,4,4a,9,10,10a(trans-4a,10a)-octahydrophenanthrenes were prepared. Permanganate oxidation of 1,2,3,4,4a,10a(trans-4a,10a)-hexahydrophenanthrene (1) afforded the 9(e),10(a) isomer, 2. Wet Prévost conditions, followed by hydrolysis, gave the 9(a),10(e) diol, 3. Opening of the syn 9,10-epoxide, 6, using trichloracetic acid in benzene, followed by hydrolysis, afforded the 9(e),10(e) diol, 4. Aqueous acid opening of anti 9,10-epoxide (7) afforded 5, the 9(a),10(a) diol. © 1974, American Chemical Society. All rights reserved.