1: 1.) DIBAH, 2.) KH / 1.) toluene, 2.) toluene and THF 2: 95 percent / KH / dimethylformamide; benzene 3: 80 percent / I2 4: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O 5: 82 percent / Na / NH3 7: 2N LiOH / methanol; H2O View Scheme

1: 1.) DIBAH, 2.) KH / 1.) toluene, 2.) toluene and THF 2: 95 percent / KH / dimethylformamide; benzene 3: 80 percent / I2 4: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O 5: 82 percent / Na / NH3 7: 2N LiOH / methanol; H2O 8: 1N NaOH / diethyl ether; H2O 9: 95 percent / DCC, HOBt, Et3N / CH2Cl2; tetrahydrofuran 10: H2 / Pd black / H2O; methanol View Scheme

1: 1.) DIBAH, 2.) KH / 1.) toluene, 2.) toluene and THF 2: 95 percent / KH / dimethylformamide; benzene 3: 80 percent / I2 4: 1.) AgOAc, 2.) 1N NaOH / 1.) DMF, AcOH, 2.)MeOH, H2O 5: 82 percent / Na / NH3 7: 2N LiOH / methanol; H2O 8: 1N NaOH / diethyl ether; H2O View Scheme