Vibrational Circular Dichorism for Absolute Configuration of (1S,2S)-Azido Trimethylsilylcyclohexene: Useful for Muricatacin Intermediate Synthesis

• Published in: Malaysian Journal of Chemistry
• Main Author: Hussin Z.M.; Abd Haris S.A.-N.; Ghani F.S.A.; Hasan N.P.S.; Ali M.T.M.
• Format: Article
• Language: English
• Published: Malaysian Institute of Chemistry 2024
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85209935219&doi=10.55373%2fmjchem.v26i5.533&partnerID=40&md5=ea63e4a09cf73c7cdcadf2b1c13a7a64

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.