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. Author manuscript; available in PMC: 2015 Nov 5.
Published in final edited form as: J Am Chem Soc. 2015 Sep 29;137(40):12784–12787. doi: 10.1021/jacs.5b08398

SCHEME 2. Synthesis of (+)-halomon.

SCHEME 2

Reagents and conditions: a. NBS (1.05 equiv), ClTi(Oi-Pr)3 (1.10 equiv), 20 mol % (R,S)-3, hexanes, −20 °C, 73%; b. trifluoromethanesulfonic anhydride (1.2 equiv), 2,6-lutidine (1.5 equiv), CH2Cl2, −78 °C; c. L-selectride (2.2 equiv), THF, −78 °C, crude 95% from 10; d. Br2 (1.0 equiv), K2CO3 (0.1 equiv), hexanes, −78 °C; e. Lithium acetate (1.0 equiv), DMF, 0 °C; f. K2CO3 (1.0 equiv), methanol, 0 °C to r.t., 39% 12 + 22% 13; g. t-BuOCl (1.5 equiv), ClTi(Oi-Pr)3 (1.10 equiv), 30 mol % (S,R)-3, hexanes, −20 °C, 82%; h. trifluoromethanesulfonic anhydride (1.2 equiv), 2,6-lutidine (1.5 equiv), CH2Cl2, −78 °C; i. sodium hydroxide, H2O, THF, 0 °C to r.t., 69% from 14.