Synthesis of (-)-5-amino-2(3,4-dimethoxyphenyl)-4-phenyl- 1,3-dithiane

Article abstract of DOI:10.1016/S0022-2860(97)00269-X

The key intermediate of the synthesis, the (1R,2S)-1-phenyl-2-phthalimido-l,3-propanedithiol (5) was prepared from the corresponding (1S, 2S)-diol 1 in a six-step procedure. The absolute configuration of 5 followed from that of 4, which was established by X-ray crystallographic study. In reaction with veratraldehyde dithiol 5 was converted into 1,3-dithiane 6, isolated as a single isomer. The stereochemistry of the dithiane 6 was deduced from NMR spectral data analysis and MM calculations. Hydrazinolysis of 6 resulted in the title dithiane 7.