469-23-8

Usage

Uses

Eserethol is used in preparation of bisnorcymerine and its acid salt.

Upstream product

• 408508-71-4 (+/-)-5-ethoxy-1,3-dimethyl-3-(2-methylamino-ethyl)-indolin-2-one 
• 141861-84-9 (S)-5-Hydroxy-3-(3-methoxy-propyl)-1,3-dimethyl-1,3-dihydro-indol-2-one 
• 133343-18-7 (3S)-3-(2-carboxyethyl)-5-ethoxy-1,3-dimethyl-2-oxindole 
• 133343-16-5 (3S)-5-ethoxy-3-(3-methoxypropyl)-1,3-dimethyl-2-oxindole 
• 133343-15-4 (3S)-3-(3-methoxypropyl)-7-methoxy-1,3-dimethyl-5-oxohexahydro-2-oxindole 
• 133343-17-6 (3S)-5-ethoxy-3-(3-hydroxypropyl)-1,3-dimethyl-2-oxindole 
• 141861-82-7 (3S)-3-(3-methoxypropyl)-7-methoxy-1,3-dimethyl-5-methylenehexahydro-2-oxindole 
• 64-17-5 ethanol 
• 133343-19-8 (3S)-5-ethoxy-3-(2-ethoxycarbonylaminoethyl)-1,3-dimethyl-2-oxindole 
• 69926-96-1 d,l-eserethole 

Downstream Products

• 139314-01-5 (3aS,cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 469-22-7 eseroline 

Relevant academic research and scientific papers

A formal asymmetric synthesis of Calabar bean alkaloids

A total synthesis of (-)-eserethole (2) has been accomplished using the Diels-Alder reaction of (S)-(-)-methyl-2-[2-(E)-nitroethenyl]-δ- valerolactone (3) and Danishefsky's diene as a key step. The synthesis of optically pure (-)-eserethole (2) constitutes a formal synthesis of naturally occurring Calabar bean alkaloids such as (-)-physostigmine (1), (-)- physovenine (17) and (-)-geneserine (18).

A Chiral Total Synthesis of (-)-Physostigmine

A chiral total synthesis of (-)-physostigmine via (-)-eserethole has been achieved starting from (S)-(-)-2-methyl-2-(2'-nitrovinyl)-δ-valerolactone.