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. Author manuscript; available in PMC: 2013 Aug 19.
Published in final edited form as: J Am Chem Soc. 2013 Jul 11;135(29):10634–10637. doi: 10.1021/ja405833m

Scheme 4.

Scheme 4

Synthesis of benzooxepanes and benzoazepinonesa

aReaction conditions: (a) Me2S-BH3, THF; 85%. (b) TsCl, Et3N, CH2Cl2. (c) NaH, THF; 53% both steps. (d) H2SO4, MeOH; 74%. (e) Tf2O, DCM; 99%. (f) Pd(OAc)2, rac-BINAP, Cs2CO3, H2N(CH2)2N(CH3)2, THF; 91%. (g) aq. LiOH, THF; then HBTU, i-Pr2EtN, DMF, 65% (as the HCl salt)