860438-75-1

Upstream product

• 21339-55-9 1-methyl-L-tryptophan 
• 860438-73-9 1-methyl-3-[(2S)-1-(toluene-4-sulfonyl)aziridin-2-ylmethyl]-1H-indole 
• 860617-73-8 N-[(1S)-1-(1-benzenesulfonyl-3,4-dihydroxycyclopentylmethyl)-2-(1-methyl-1H-indol-3-yl)ethyl]-4-methylbenzenesulfonamide 
• 860438-74-0 N-[(1S)-1-(1-benzenesulfonylcyclopent-3-enylmethyl)-2-(1-methyl-1H-indol-3-yl)ethyl]-4-methylbenzenesulfonamide 

Downstream Products

• 860438-76-2 (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.0^2,10.0^4,9]hexadeca-2⁽¹⁰⁾,4,6,8,13-pentane 

Relevant academic research and scientific papers

4-(Phenylsulfonyl)-4-lithiocyclopentene as a nucleophilic 2-pentene-1,5-dial synthetic equivalent. An aziridine-based synthetic approach to (-)-alstonerine

Reaction of 4-lithio-4-(phenylsulfonyl)cyclopentene with an l-tryptophan-derived N-tosylaziridine provides an adduct. Oxidative cleavage of the cyclopentene double bond provides a dialdehyde, which enters into acid-catalysed Pictet-Spengler-type bicyclisation to give a tetracyclic aldehyde. Completely regioselective silyl dienol ether formation followed by completely stereoselective hetero-Diels-Alder reaction with monomeric formaldehyde gives a late-stage intermediate in a planned total synthesis of the macroline-related alkaloid (-)-alstonerine.