171925-90-9

Upstream product

• 100-39-0 benzyl bromide 
• 223907-24-2 Methyl (4aS,5R,6S,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-(benzyloxymethyl)perhydronaphthalene-1-carboxylate 
• 223907-23-1 Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate 
• 223907-22-0 Methyl (2Z,6E)-3[(diethoxyphosphoryl)oxy]-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]nona-2,6-dienoate 
• 223907-20-8 Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate 
• 223907-19-5 (2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane 
• 116179-52-3 (-)-6,7-epoxy-8-(benzyloxy)geranyl alcohol 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 171925-89-6 Trifluoro-methanesulfonic acid (4aS,5R,6S,8aS)-6-benzyloxy-5-benzyloxymethyl-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 1027024-89-0 C₂₉H₃₈O₄ 
• 172018-08-5 (4aS,5R,6S,8aS)-6-Benzyloxy-5-benzyloxymethyl-5,8a-dimethyl-octahydro-naphthalen-1-one 
• 172018-07-4 C₁₁H₁₄O₂C₂H₄OC₂H₆OH₂ 
• 389103-83-7 (4a'R,5'R,8a'S)-5'-(hydroxymethyl)-5',8a'-dimethylhexahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one 

Downstream Products

• 171925-91-0 (4aR,5R,6S,8aS)-6-Benzyloxy-5-benzyloxymethyl-2,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 171925-92-1 (3S,4aR,5R,6S,8aS)-6-Benzyloxy-5-benzyloxymethyl-3-hydroxy-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 147444-03-9 α-pyronemeroterpenoid pyripyropene A 

Relevant academic research and scientific papers

A formal synthesis of (+)-pyripyropene A using a biomimetic epoxy-olefin cyclisation: Effect of epoxy alcohol/ether on cyclisation efficiency

The synthesis of the decalin sub-unit 2 of (+)-pyripyropene A 1 (a key intermediate in the first total synthesis) is described. The key step involves a biomimetic epoxy-olefin cyclisation using an allylsilane as the terminating group. Whilst attempts to cyclise epoxy alcohol 6 were unfruitful, cyclisation of the protected epoxy benzyl ether 7 using BF3·OEt2 was successful, yielding bicyclic ester 25. Isomerisation of the exocyclic double bond into conjugation with the ester group proved to be problematic, although successful conditions were ultimately found. The Royal Society of Chemistry 1999.