in water T=30°C; biotransformation by Pseudomonas putida monooxygenase; pH 7.1; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

in water T=30°C; biotransformation by Pseudomonas putida monooxygenase; pH 7.1; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 60 percent / N-bromosuccinimide (1 equiv) / 23 °C / acetone-water (5:1) 2: 67 percent / 30 percent H2O2 / acetic acid / 4 h / 5 °C 3: 92 percent / 1.15 equiv Bu3SnH / 0.2 equiv bisazoisobutyronitrile / benzene / 24 h / Heating 4: 1.) dimethyl sulfoxide (1.1 equiv), (CF3CO)2O / 1.) CH2Cl2, -65 deg C, 2.) Et3N, 25 deg C, 1 h 5: K2CO3 / dimethylformamide / 48 h / 23 °C 6: 1.) CpZrHCl, 2.) Ni(acac)2, diisobutylaluminium hydride / 1.) THF, 0 deg C, 2.) THF, -10 deg C then 0 deg C, 8 h 7: 1.) Li-sec-Bu3BH (L-Selectride), 2.) tosic acid / 1.) THF, -78 deg C, 2 h, 2.) toluene, reflux, 10 h 8: 97 percent / diisopropylethylamine / CH2Cl2 / 10 h / 23 °C 9: 98 percent / i-Bu2AlH / CH2Cl2 / 1.5 h / -78 °C 10: 94 percent / piperidine / acetonitrile / 48 h / 5 °C 11: 90 percent / diisopropylethylamine / CH2Cl2 / 23 °C 12: 87 percent / HOAc, H2O (3:1) / 5 h / 23 °C 13: 93 percent / 0.15 M LiOH / 24 h / 23 °C / MeOH, H2O (6:1) 14: 1.) lactonization, 2.) MEM ether cleavage View Scheme

in water T=30°C; biotransformation by Pseudomonas putida monooxygenase; pH 7.1; Yield given. Yields of byproduct given. Title compound not separated from byproducts;