Beilstein J. Org. Chem.2010,6, No. 69, doi:10.3762/bjoc.6.69
treatment with tert-butyl(dimethyl)silyl chloride gave alcohol 4 in 59% yield after removal of the doubly silylated side product the formation of which could not be completely avoided. By means of an Appelreaction [15], the alcohol 4 was converted into the bromide 5 in 79% yield. In the following key-step
Beilstein J. Org. Chem.2008,4, No. 31, doi:10.3762/bjoc.4.31
reaction with lithium cyclohexyl(isopropyl)amide (LCIA) in 49% overall yield for the 4-step sequence. The elaboration of intermediate 27 entailed a protection-deprotection maneuver that prepared the molecule for an ultimate Appelreaction [28] as a way to install the iodo substituent. The second key