179939-68-5

Upstream product

• 66087-99-8 (3S)-3-amino-4-(1H-indol-3-yl)butanenitrile 
• 179939-65-2 (1S,3S)-2-Benzyl-3-cyanomethyl-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole 
• 179939-64-1 (1S,3S)-2-Benzyl-3-cyanomethyl-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 179939-63-0 (1S,3S)-3-Cyanomethyl-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 179939-66-3 (1S,3S)-2-Benzyl-3-cyanomethyl-1-(2-hydroxyethyl)-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole 
• 318276-43-6 (1S,3S)-2-Benzyl-3-cyanomethyl-1-formylmethyl-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole 
• 179939-67-4 (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-2-ethyl-but-2-enenitrile 

Downstream Products

• 143120-75-6 (-)-N_b-benzylsuaveoline 

Relevant academic research and scientific papers

The total synthesis of (-)-suaveoline

A new synthesis of the indole alkaloid (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described. The Royal Society of Chemistry 2000.

A total asymmetric synthesis of (-)-suaveoline

A new total synthesis of (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%); key steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons/alkylation procedure, a vinylogous Thorpe cyclization