110815-27-5

Upstream product

• 108-24-7 acetic anhydride 
• 2717-76-2 (S)-N-benzyloxycarbonyl-L-tryptophan methyl ester 
• 501-53-1 benzyl chloroformate 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 61535-47-5 benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 
• 75-36-5 acetyl chloride 

Downstream Products

• 131442-94-9 (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 84590-48-7 (+)-Epi-indolactam-V 
• 110815-33-3 2-[3-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 110815-30-0 Acetic acid (R)-2-benzyloxycarbonylamino-3-(6-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-29-7 Acetic acid (R)-2-benzyloxycarbonylamino-3-(4-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-31-1 Acetic acid (R)-3-(4-amino-1H-indol-3-yl)-2-benzyloxycarbonylamino-3-oxo-propyl ester 
• 110815-32-2 (S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 84590-48-7 indolactam V 
• 110815-28-6 (R)-(1-((acetoxy)methyl)-2-(1H-indol-3-yl)-2-oxoethyl)carbamic acid phenylmethyl ester 

Relevant academic research and scientific papers

A Regio- and stereocontrolled total synthesis of (-)-indolactam-V

(-)-Indolactam-V (IL-V) (1)-was prepared in 10 steps from L-tryptophan methyl ester in 17.1% overall yield. The key steps involve regiospecific thallation of the acylindole intermediate (4), followed by azide displacement and reduction to introduce the 13-amino group. Control of the C-11 stereocenter was achieved by SN2 displacement of the chiral inflate (10), derived from D-valine. The thallium mediated closure of dipeptide (17) did not provide an alternative route to IL-V.

SYNTHETIC STUDIES ON TELEOCIDIN IV. AN EFFICIENT SYNTHESIS OF (-)-INDOLACTAM V

An efficient synthesis of (-)-indolactam V (3) was achieved in 12 steps starting from L-tryptophan.