185394-47-2

Upstream product

• 185394-44-9 (1aS,3aR,5S,6aR,6bS)-3a-Benzoyloxy-1a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,4,5,6a,6b-hexahydro-1-oxa-6-aza-cyclopropa[e]indene-5,6-dicarboxylic acid 6-benzyl ester 5-methyl ester 
• 185394-45-0 (2S,3aR,7S,7aR)-3a-Benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-oxo-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 185394-43-8 (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 108-24-7 acetic anhydride 
• 185394-46-1 (2S,3aR,6R,7S,7aR)-3a-Benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 

Relevant academic research and scientific papers

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

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.