136569-50-1

Upstream product

• 108-24-7 acetic anhydride 
• 136569-47-6 C₁₈H₂₁NO₂ 
• 74-88-4 methyl iodide 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 136569-48-7 C₂₀H₂₃NO₃ 
• 136656-41-2 (2R,3aS,4R,7S,7aR)-2-Methyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one 
• 136569-49-8 N-[4-Methoxy-2-((2S,3aS,4R,7S,7aR)-2-methyl-1-oxo-2,3,3a,4,7,7a-hexahydro-1H-4,7-methano-inden-2-yl)-phenyl]-N-methyl-acetamide 
• 139685-68-0 (3aS,4R,7S,7aR)-2-Methyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one 

Relevant academic research and scientific papers

7,7-Dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of ketodicyclopentadiene: A new route to (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine

A new diastereocontrolled route to three alkaloids having a quaternary benzylic stereogenic center, (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine, has been developed using enantiopure 7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of chiral cyclopentadienone.

Enantiocontrolled Total Syntheses of (-)-Physovenine and (-)-Physostigmine

Enantiocontrolled total syntheses of the Calabar bean alkaloid (-)-physovenine (1) and (-)-physostigmine (2) have been achieved in a concise manner starting from the optically active tricyclic enone 3 employing a Fischer indolization reaction under nonacidic conditions as the key step.