88196-82-1

Upstream product

• 88125-72-8 7α-methyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>dec-3-en-2-one 
• 106539-60-0 5,6-dihydro-6-(4-methylpent-4-enyl)-5-oxo-2H-pyran-2-yl acetate 
• 88125-70-6 1-(2-furyl)-5-methylhex-5-en-1-ol 
• 106539-86-0 4β-isopropyl-7α-methyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>decan-2-one 
• 88125-71-7 6-hydroxy-2-(4-methylpent-4-enyl)-2H-pyran-3(6H)-one 
• 41182-50-7 5-bromo-2-methyl-1-pentene 
• 88125-73-9 4β-isopropyl-2β,7α-dimethyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>decan-2α-ol 

Relevant academic research and scientific papers

Synthesys of (+/-)-Cryptofauronol and Related Valerane Sesquiterpenes via Rearrangement of Bicyclodecane Precursors

Alkenyl-substituted furfuryl alcohols have been converted into the corresponding alkenyl-substituted pyrylium species which undergo intramolecular cycloaddition to produce highly functionalised perhydroazulenes.These products, epoxybicyclodecanones and the corresponding alcohols, can undergo acid-catalysed rearrangement reactions to give cis-fused bicyclodecanes.The scope and limitations of these rearrangement reactions have been explored.The process has been adapted for use in the synthesis of the sesquiterpenes (+/-)-cryptofauronol, (+/-)-fauronyl acetate, (+/-)-valeranone, and (+/-)-valerane.

Total Synthesis of (+/-)-β-Bulnesene, (+/-)-Cryptofauronol, (+/-)-Fauronyl Acetate, and (+/-)-Valeranone

A versatile method for the preparation of perhydroazulenes and cis-fused 1-decalones is described and exemplified by the synthesis of the title compounds.