Stereodivergent routes from tyrosine to the 7-(R) and 7-(S) diastereomers of the 7-hydroxy-2,3,7,7a-tetrahydroindole ring found in gliotoxin

Article abstract of DOI:10.1016/0040-4020(96)00871-X

Two routes from the oxidative cyclization product 1 derived from tyrosine to methyl 7-(tert-butyldimethylsiloxy)-N-(benzyloxycarbonyl)-2,3,7,7a-tetrahydro indole-2-carboxylate are described. The routes are stereodivergent leading to the 2-S,7-S,7a-S (6) and 2-S,7-R,7a-S-(13) diastereomers. The former stereochemistry corresponds to that present in gliotoxin.