10.1016/j.tetlet.2011.07.035
The research presents a stereoselective synthesis of the naturally occurring pyrrolidine alkaloid, (+)-radicamine B, which possesses significant biological properties. The synthesis involves 13 steps, starting from commercially available p-hydroxybenzaldehyde, with an overall yield of 9.75%. Key reactions include Sharpless asymmetric epoxidation and Horner–Wadsworth–Emmons (HWE) olefination. Reactants used throughout the synthesis include p-hydroxybenzaldehyde, tosyl chloride, (+)-DET, NaN3, PPh3, Boc anhydride, benzaldehyde dimethylacetal, DIBAL-H, IBX, (OEt)2PO(CH2COOEt), and (+)-DIPT, among others. Analytical techniques employed to characterize the intermediates and final product included 1H NMR, 13C NMR, Mass spectrometry, and IR spectroscopy, with enantioselectivity determined by chiral HPLC. The study also discusses the biological significance of radicamine B and the challenges in its asymmetric synthesis, highlighting the efficiency and linearity of their developed synthetic protocol.
10.1021/jo0013711
The research focuses on the asymmetric synthesis of (S)-CPPG, a selective antagonist for group III metabotropic glutamate receptors (mGluRs), which are important in studying neurotransmission mechanisms. The synthesis begins with (R)-4-benzoxyphenylglycine and involves several steps including protection of the amino group, formation of trans-oxazolidinone, introduction of a dicarbon functional group, and cyclopropanation. Key reactants include methyl chloroformate, benzaldehyde dimethyl acetal, boron trifluoride etherate, and various catalysts for cyclopropanation. The process involves recrystallization, HPLC, and 1H NMR for analysis, and culminates in the production of (S)-CPPG with a final yield of 99% after purification. The study also mentions the biological evaluation of the synthesized compound, indicating ongoing research into its physiological effects.