Synthesis of 1-Deoxycastanospermin and Stereoisomers

Article abstract of DOI:10.1021/jo00037a025

Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized.Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization.The aminotriols were obtained in good yields with a concise overall sequence.