77204-60-5

Upstream product

• 17642-90-9 1-benzylhexahydro-2H-azepine-2-thione 
• 109741-18-6 1-benzyl-4,5,6,7-tetrahydro-1H-azepine-3-carbaldehyde 
• 100-39-0 benzyl bromide 
• 109741-21-1 (E)-4-(1-benzyl-2-dimethoxymethylpiperidin-2-yl)-3-buten-2-one 
• 109741-17-5 1-benzyl-2-methylthio-4,5,6,7-tetrahydro-1H-azepine-3-carbaldehyde 
• 109741-20-0 1-benzyl-2-dimethoxymethylpiperidine-2-carbaldehyde 
• 109741-16-4 1-benzyl-2-thioxohexahydroazepine-3-carbaldehyde 

Downstream Products

• 88204-70-0 1-Benzyl-7-butyl-9-trimethylsilanyloxy-1-aza-spiro[5.5]undec-8-ene 
• 86817-86-9 O-acetyl-N-benzyldepentylperhydrohistrionicotoxin 
• 86817-86-9 O-acetyl-N-benzyldepentylperhydrohistrionicotoxin 
• 55228-77-8 (6R,7R,8R)-7-Butyl-1-aza-spiro[5.5]undecan-8-ol 
• 88204-71-1 1-benzyl-7-butyl-1-azaspiro<5.5>undec-7-en-9-one 
• 88204-72-2 1-benzyl-7-butyl-1-azaspiro<5.5>undec-7-en-9-ol 
• 83562-28-1 1-benzyl-7-butyl-1-azaspirocyclo<5.5>undec-7-ene 
• 83562-31-6 (6RS,7SR,8SR)-7-n-Butyl-N-benzyl-1-azaspiro<5.5>undecan-8-ol 
• 83602-28-2 (6RS,7RS,8RS)-7-n-Butyl-N-benzyl-1-azaspiro<5.5>undecan-8-ol 
• 55228-77-8 (+/-)-depentylperhydrohistrionicotoxin 

Relevant academic research and scientific papers

SYNTHESIS OF AZASPIROCYCLIC COMPOUNDS VIA ORGANOIRON COMPLEXES. POTENTIAL SYNTHETIC ROUTES TO HISTRIONICOTOXIN AND CEPHALOTAXUS ALKALOIDS

Reaction of cyclohexadienylium-Fe(CO)3 complexes (7) and (8) with sodiomalononitrile gives the carbo-spirocyclic derivatives (9) and (10), whilst reaction with benzylamine and removal of iron leads to the azaspirocyclic enones (15) and (16), respectively.

A short formal synthesis of (±)-perhydrohistrionicotoxin

The reaction of a silyl enol ether bearing a nitrogen atom with a hemiacetal vinylog in the presence of a catalytic amount of boron trifluoride etherate led to the corresponding ketoaldehyde. The cyclisation of the ketoaldehyde into azaspiroenone and nitrogen deprotection was performed in basic medium. The N-benzylation of this enone gave the known key intermediate of total synthesis of (±)-perhydrohistrionicotoxin. Georg Thieme Verlag Stuttgart.

New Piperidinic Synthons via Ring Contraction. Formal Synthesis of (+/-)-Perhydrohistrionicotoxin

The 2,2-bifunctionalized piperidines 6 and 10 were obtained via ring contraction of the seven-membered heterocyclic enamino aldehyde 5 in nearly quantitative yield.The synthesis of 1-benzyl-1-azaspiroundec-7-en-9-one 9 (a formal precursor or perhydrohistrionicotoxin 1b) in 3 steps from the piperidinedialdehyde monoacetal 6, is reported.

Organoiron Complexes in Organic Synthesis. Part 18. Spiroannelation Reactions of some Bifunctional Tricarbonyl(cyclohexadienyl)iron Hexafluorophosphate Salts

The synthesis of tricarbonyl(cyclohexadienylium)iron salts containing tosyloxy-substituents in the lateral chain, and their reactions with nucleophiles to give spirocyclic compounds, is described.The synthesis and spiroannelation reactions of complexes wi