377779-92-5

Upstream product

• 184434-21-7 2-methyl-2-(1-methylindol-3-yl)propionaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 2179-92-2 tri-n-butyltin cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 406500-63-8 2-hydroxy-3-methyl-3-(1-methylindol-3-yl)butyronitrile 
• 603-76-9 1-methylindole 

Relevant academic research and scientific papers

Asymmetric synthesis of the highly methylated tryptophan portion of the hemiasterlin tripeptides

(equation presented) The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asy

A total synthesis of (-)-hemiasterlin using N-Bts methodology

A total synthesis of (-)-hemiasterlin has been accomplished in nine steps from 258 (>35% yield overall). An improved enantiocontrolled route to the tetramethyltryptophan subunit 32 was developed using an asymmetric Strecker synthesis (five steps, 50% yield from 25), and the dipeptide 22 was prepared in seven steps, 37% yield from valinol. The synthesis exploits the high reactivity of a Bts-protected amino acid chloride in the difficult peptide coupling of sterically hindered amino acid residues 18 and 20 to form 21 (70%, recrystallized) and also uses N-Bts intermediates for the high-yielding N-methylations of 14 and 31. In addition, the Bts-protected di-tert-butyl N-acylimidodicarbonate 33 is shown to undergo efficient coupling with 22 to form 34 (97% in the coupling step; 79% over the activation; coupling sequence from 32).