1: 79 percent / Pd(Cl)2(PPh3)2 / 5 h / 100 °C 2: 1) 3N HCl, 2) TsOH*H2O / 1) EtOH, r.t., 24 h, 2) C6H6, reflux, 30 min. View Scheme

1: 1-bromo-2-(methoxymethyloxy)benzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; Inert atmosphere; 2: (S)-6,8-bis(methoxymethoxy)-3-methylisochroman-1-one in tetrahydrofuran; hexane T=-78°C; 1 h; Inert atmosphere;

1: 71 percent / 2 M aq.Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol / 18 h / Heating 2: 1) BBr3, 2) glacial HOAc / 1) CH2Cl2, overnight, 2) reflux, 8 h View Scheme

1: 1) 1.4M sec-BuLi in hexane, 2) ZnBr2, 3) PdCl2(dppf) / 1) THF, 1 h, -78 deg C, 2) THF, hexane, -78 deg C, 15 min then -78 deg C to RT, 3) THF, hexane, 48 h, RT 2: 2N HCl / methanol / Heating View Scheme

1: With n-butyllithium in diethyl ether T=-65°C; 1.16667 h; Inert atmosphere; 2: With boron triethoxide in diethyl ether T=-65°C; 1 h; Inert atmosphere;

n-butyllithium in diethyl ether; hexane under Ar atm.; Et2O cooled to -65°C; n-BiLi in hexane added slowly to stirred solvent; bromide dropped; mixt. stirred for 1 h at -65°C; (EtO)3B dropped; mixt. stirred for 1 h at -65°C; H2SO4 quickly added; temp. rose until about 20; phases sepd.; aq. phase extd. (Et2O); solvent (about 3/4 vol.) removed (vac.); H2O added; evapd. for 0.5 h; aq. phase removed by decantation; hexane added; slurry kept at 4°C for 11 d; solid filtered off; dissolved (acetone/H2O); standing at room;