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. Author manuscript; available in PMC: 2012 Jan 1.
Published in final edited form as: Medchemcomm. 2011 Jan 1;2(9):904–908. doi: 10.1039/C1MD00040C

Scheme 3.

Scheme 3

Synthesis of the C1–C14 unit. Reagents and conditions: a) (−)-Ipc2BOMe, Allylmagnesium bromide, diethyl ether, 89%; b) 19, 2,4,6-trichloro benzoylchloride, Et3N, DMAP, 88%, 1:1 diastereomers; c) 2nd generation Hoveyda-Grubbs catalyst, 49%, 3:2 diastereomers; d) i. PPTS, MeOH, 80 °C, 66%; ii. Et3N, Ac2O, DMAP, quant; e) i. DDQ, CH2Cl2, 70%; ii. Dess-Martin periodinane, CH2Cl2, 95%.