66405-83-2

Upstream product

• 115171-41-0 2-ethoxycarbonyloxy-3,4-dihydro-6-methoxy-1-methyl-naphthalene 

Downstream Products

• 115522-83-3 3-(2-acetyl-5-methoxyphenyl)propionic acid methyl ester 
• 115522-85-5 2-[4-Methoxy-2-(3-oxo-propyl)-phenyl]-acrylonitrile 
• 115522-87-7 (E)-5-<2-(1-cyanovinyl)-5-methoxyphenyl>-1-hydroxy-2-methyl-pent-2-ene 
• 115522-84-4 methyl 3-<2-(1-cyanovinyl)-5-methoxyphenyl>propionate 
• 115522-88-8 2-[4-Methoxy-2-((E)-4-methyl-5-oxo-pent-3-enyl)-phenyl]-acrylonitrile 
• 115522-86-6 (E)-ethyl 5-<2-(1-cyanovinyl)-5-methoxyphenyl>-2-methylpent-2-enoate 
• 115522-89-9 (E)-6-<2-(1-cyanovinyl)-5-methoxyphenyl>-2-hydroxy-3-methyl-1-trimethylsilylhex-3-ene 
• 115522-94-6 (4aS*)-4aα-(N-benzylaminomethyl)-3,4,4a,9,10,10aα-hexahydro-7-methoxy-1-methylphenanthrene 
• 115522-94-6 (4aS*)-4aα-(N-benzylaminomethyl)-3,4,4a,9,10,10aβ-hexahydro-7-methoxy-1-methylphenanthrene 
• 115522-92-4 (4aS*)-4aα-(benzamidomethyl)-3,4,4a,9,10,10aα-hexahydro-7-methoxy-1-methylphenanthrene 
• 115522-92-4 (4aS*)-4aα-(benzamidomethyl)-3,4,4a,9,10,10aβ-hexahydro-7-methoxy-1-methylphenanthrene 

Relevant academic research and scientific papers

Use of an Electrocyclic Reaction of o-Quinodimethane and an Intramolecular Mannich-type Cyclisation in Diterpene Alkaloid Synthesis: a Synthesis of Nagata's Intermediate for (+/-)-Atisine

A synthesis of the tetracyclic amine hydrochloride (2), a pivotal intermediate for Nagata's total synthesis of (+/-)-atisine, is described.The synthesis commenced with an electrocyclic reaction of the Z-o-quinodimethane (10), generated in situ by thermolysis of the benzocyclobutene (9), leading to the dihydronaphthalene (8).The hydrophenanthrene portion in (2) was elaborated by an intramolecular Diels-Alder reaction of the transient triene (6), which was produced from (8) via a nine-step sequence.The piperidine ring construction was accomplished by employing an intramolecular Mannich-type cyclisation (or an intramolecular iminium-ene reaction) of the hydrochloride (4); the resulting tetracycle (3) was then finally converted into (2) by catalytic hydrogenation.The cis-hydrochloride (27) was similarly converted into the cis-tetracycle (31) via (30), whose structure was established by a single-crystal X-ray analysis, by the same manner.

Novel Synthesis of a Key Intermediate for (+/-)-Atisine

A novel synthesis of Nagata's tetracyclic intermediate (2) for (+/-)-atisine (1) has been accomplised from the benzocyclobutene (3) via two newly developed methodologies.