185394-34-7

Upstream product

• 144534-49-6 (2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 

Downstream Products

• 185394-35-8 (2S-(2β,3aβ,6α,7aβ))-2,3,3a,6,7,7a-hexahydro-6-acetyloxy-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester 
• 185394-37-0 (1S,2R,4S,6S,7R)-6-Hydroxy-8,9-dioxa-3-aza-tricyclo[5.2.2.0^2,6]undec-10-ene-3,4-dicarboxylic acid 3-benzyl ester 4-methyl ester 
• 185394-36-9 (2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester 

Relevant academic research and scientific papers

Synthesis of hydroxylated bicyclic amino acids from L-tyrosine: Octahydro-1H-indole carboxylates

(Chemical Equation Presented) A stereoselective approach to polyhydroxylated L-Choi derivatives has been developed. The oxidative cyclization of L-tyrosine was optimized to avoid partial racemization and to allow a more efficient scale-up.

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.