76036-00-5

Upstream product

• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 26808-45-7 2,8α-dimethyl-7α-bicyclo<5.3.0>dec-1-en-5-one 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 98-01-1 furfural 
• 51174-44-8 3-methyl-4-penten-1-ol 
• 7796-71-6 3-methyl-4-pentenoic acid ethyl ester 
• 88125-64-8 8α-methyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>dec-3-en-2-one 
• 88125-75-1 8-methyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>decan-2-ones 
• 88125-67-1 2,8β-dimethyl-7α-bicyclo-<5.3.0>dec-2-en-5β-ol 
• 88125-63-7 6-acetoxy-2-(3-methylpent-4-enyl)-2H-pyran-3(6H)-one 
• 88125-62-6 6-hydroxy-2-(3-methylpent-4-enyl)pyran-3(6H)-one 
• 88125-61-5 2-(1-hydroxy-4-methylhex-5-enyl)furan 
• 88125-65-9 2β,8-dimethyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>decan-2α-ol 

Relevant academic research and scientific papers

Total Synthesis of (+/-)-β-Bulnesene via Intramolecular Cycloaddition of a 2-Substituted 3-Oxidopyrylium

A route to the sesquiterpene (+/-)-β-bulnesene is described which starts with the substituted furan, 2-(1-hydroxy-4-methylhex-5-enyl)furan.Oxidation of the latter generates a precusor of a 2-substituted 3-oxidopyrylium, which undergoes smooth intramolecular cyclisation to generate a highly functionalised perhydroazulene intermediate.Further chemical manipulation of the latter readily generates the desired natural product.In order to control the relative geometry of the pendent-4-methyl group in the target molecule, a method involving the stereoselective reduction of an exocyclic methylene group is employed; the means for introducing such methylene groups are detailed.

Facile approach to the bicyclo[5.3.0]decane ring system; efficient synthesis of (±)-7-epi-β-bulnesene

An efficient strategy for the rapid construction of the guiane bicyclo[5.3.0]decane ring system from appropriately substituted 4-alkyn-1-ols has been developed. This methodology relies on a MeLi-catalyzed tandem 5-exo-dig cyclization/Claisen rearrangement sequence as the key ring forming step.

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.

Total Synthesis of β-Bulnesene and 1-Epi-β-bulnesene by Intramolecular Photoaddition

dl-β-Bulnesene (1) and dl-1-epi-β-bulnesene (15) have been synthesized starting from the bromine 4 (Shemes 2 and 3).In the key step 9->10 the bonds of the final product were formed by an interamolecular photoaddition.The synthesis was completed by the fragmentation 12->14 and the Wittig reaction 14->15+1.