141613-08-3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1215-59-4 5-benzyloxy-1H-indole 
• 21987-24-6 5-(benzyloxy)-3-methyl-1H-indole 
• 141613-07-2 (R)-3-(isopropylsulfinyl)oxazolidin-2-one 
• 141612-97-7 tert-butyl 5-(benzyloxy)-3-methyl-1H-indole-1-carboxylate 

Downstream Products

• 141661-45-2 (-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one 
• 141613-01-6 (+)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one 
• 141613-16-3 5-(benzyloxy)-8-(tert-butoxycarbonyl)-3,3-dichloro-3a-methyl-8a-<(2-propyl)sulfenyl>-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one 

Relevant academic research and scientific papers

The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides

The total synthesis of naturally occurring (-)-physostigmine is described. The key element for the asymmetric induction is the chirality transfer from optically active 2-(alkylsulfmyl)indoles to indoline butyrolactones bearing two chiral centers. Novel features of this synthesis involve the use of a new class of sulfoxylating agents, N-(alkylsulfinyljoxazolidinones, to prepare the starting indolyl sulfoxides and the correlation of the size of the alkyl group on the sulfoxide with the degree of asymmetric induction. The overall synthesis requires a dozen steps from commercially available 5-(benzyloxy)indole.