| Summary: | A simple technique for absolute configuration determination of (1S,2S)-azido trimethylsilylcyclohexene 3 enantiomer is described. Samples were synthesized from racemic monoepoxide 1, via asymmetric epoxide ring opening catalyzed by (R,R)-salen complex, L-2 in the presence of trimethyl silylazide, TMSN3. (1S,2S)-azido trimethylsilylcyclohexene 3 and its corresponding racemic adduct were analyzed using VCD spectrometer. The VCD spectrums of boths compounds were recorded as linear regressions (dABS.) vs wavenumbers (cm-1). The major selected bands were analyzed to determine the absolute configuration of (1S,2S)-azido trimethylsilylcyclohexene 3. Compound 3 then underwent reduction and protection sequence to give 4. Allylic hydroxylation of 4 gave rise to compound 5 which was subjected to oxidative cleavage and lactonization steps that successfully afforded Muricatacin intermediate 6. © 2024 Malaysian Institute of Chemistry. All rights reserved.
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