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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 1. Synthesis of (−)-plocamenone and (−)-isoplocamenone.

SCHEME 1

Reagents and conditions: a. NBS (1.05 equiv), ClTi(Oi-Pr)3 (1.10 equiv), 20 mol % (S,R)-3, hexanes, −20 °C, 64%; b. Dess–Martin periodinane (DMP) (1.5 equiv), NaHCO3 (10.0 equiv), CH2Cl2, r.t.; c. diethyl (1-chloro-2-oxobutyl)phosphonate (6) (2.0 equiv), sodium hexamethyl-disilazide (NaHMDS) (1.4 equiv), THF, −78 °C to 0 °C, 70% from 5; d. trimethylsilyl trifluoromethanesulfonate (TMSOTf) (2.0 equiv), N,N-diisopropylethylamine (3.0 equiv), CH2Cl2, −78 °C to r.t.; 8 (5.0 equiv), −78 °C to r.t.; e. iodomethane (5.0 equiv), N,N-diisopropylethylamine (3.6 equiv), THF, r.t., 54% from 7; f. floodlamp, Et2O, 5 days, r.t.