a BH3·Me2S, 99%. b DMP oxidation, 96%. c (-)-Ipc2B-allyl, 87%. d Me2NH, EtOH, 98%. e Acrolein-diethylacetal, TsOH, toluene, 92%. f 4 mol% Grubbs catalyst, CH2Cl2, 87%. g CH2 = CHOTBS, LiClO4, 92%. h (1) NaBH4, MeOH, 0 °C, 99%; (2) TESCl, py, 92%. i MeLi, Et2O, −75 °C, 90%. j KHMDS, C6H5NTf2, THF, 80%. k 5 mol% Pd(PPh3)4, LiCl (5 equiv), TMSCH2MgBr (2 equiv), Et2O, 96%. l K2CO3, MeOH, 0 °C, 98%. m DMP oxidation 90%
Coupling of the two fragments 165 and
166 by Julia chemistry involved lithiation of
166 and treatment of the resulting dianion with
aldehyde 165 (Scheme 25).
The building block 184 was synthesized starting
from the commercially available ethyl hydrogen
(R)-3-methylglutarate 186 (Scheme 25) and
transformed to the homoallylic alcohol 187 by
reduction, oxidation, asymmetric Brown allylation [139, 152,
158–160 ] and dimethyl amide formation.
Final removal of the TES group and subsequent oxidation led to the
C3–C14 fragment 184 (Scheme 25). .
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