3772-93-8

Upstream product

• 88125-64-8 8α-methyl-1β,5β-epoxy-1β,7α-bicyclo<5.3.0>dec-3-en-2-one 
• 51174-44-8 3-methyl-4-penten-1-ol 
• 98-01-1 furfural 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 26808-45-7 2,8α-dimethyl-7α-bicyclo<5.3.0>dec-1-en-5-one 
• 22451-73-6 2-(3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydro-5-azulenyl)-2-propanol 
• 7796-71-6 3-methyl-4-pentenoic acid ethyl ester 
• 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

Revisiting the Chemistry of Guaiacwood Oil: Identification and Formation Pathways of 5,11- and 10,11-Epoxyguaianes

Guaiacwood oil from Bulnesia sarmientoi Lorentz ex. Griseb is a common natural ingredient of the perfume industry used in both domestic and luxury fragrances for its highly appreciated woody-rosy odor, as well as its excellent fixative properties. Despite its long and traditional use as a perfume ingredient, guaiacwood oil has not been extensively studied. Thus, the chemical characterization of its constituents by using a full array of GC-hyphenated techniques (GC-MS, GC × GC-MS, and pc-GC) combined with conventional chemical fractionation was undertaken. In the course of this work, 15 new sesquiterpenoids mostly belonging to the 5,11- and 10,11-epoxyguaiane families were identified. Each isolated compound was fully characterized by NMR and MS. Collectively, the specific chemical relationships observed between sesquiterpene oxides and alcohols permitted the formulation of probable formation pathways regarding their presence as natural constituents of guaiacwood extracts.

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 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.

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.