52691-72-2

Usage

Uses

Used in Insect Repellent Applications:
(-)-Apoverbenone is used as a repellent against the larvae of the mosquito Aedes aegypti, a species responsible for transmitting diseases such as dengue fever, Zika virus, and yellow fever. Its natural origin and insecticidal properties make it a promising alternative to synthetic insecticides for pest control.
Used in Pest Control:
(-)-Apoverbenone is used as a natural alternative to synthetic insecticides for pest control in agriculture. Its insecticidal properties can help protect crops from various pests, reducing the need for chemical pesticides and promoting more sustainable agricultural practices.
Used in Medicinal Applications:
(-)-Apoverbenone is used for its anti-inflammatory properties, which can help alleviate inflammation and pain associated with various conditions. Its potential as a natural remedy for inflammation-related disorders makes it a valuable compound for medicinal applications.
Used in Antifungal Applications:
(-)-Apoverbenone is used for its anti-fungal properties, which can help combat fungal infections in both humans and plants. Its natural origin and potential to treat fungal infections make it a promising compound for use in antifungal medications and agricultural fungicides.

Upstream product

• 127-91-3 (1R,5R)-(+)-β-pinene 
• 77982-63-9 nopinone 
• 926645-54-7 (1S,5S)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-ol 
• 35408-03-8 (+)-apoverbenone 

Downstream Products

• 135415-66-6 4-(2-Methoxy-4-pentyl-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 54154-45-9 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene 
• 54154-46-0 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane 

Relevant academic research and scientific papers

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Synthesis of cyclobakuchiols A, B, and C by using conformation-controlled stereoselective reactions

Cyclohexanone with the pMeOC6H4 and CH 2/C(Me) substituents at the C3 and C4-positions was prepared from (+)-β-pinene and converted to the allylic picolinate by a Masamune-Wittig reaction followed by reduction and esterification. Allylic substitution of this picolinate with Me2CuMgBr×MgBr2 in the presence of ZnI2 proceeded with γ regio- and stereoselectively to afford the quaternary carbon center on the cyclohexane ring with the CH2/CH and Me groups in axial and equatorial positions, respectively. This product was converted to cyclobakuchiol A by demethylation and to cyclobakuchiol C by epoxidation of the CH2/C(Me) group. For the synthesis of cyclobakuchiol B, the enantiomer of the above cyclohexanone derived from (-)-β-pinene was converted to the cyclohexane-carboxylate, and the derived enolate was subjected to the reaction with CH2/CHSOPh followed by sulfoxide elimination to afford the intermediate with the quaternary carbon center with MeOC(/O) and CH2/CH groups in axial and equatorial positions. The MeOC(/O) group was transformed to the Me group to complete the synthesis of cyclobakuchiol B. Control is key! Synthesis of cyclobakuchiols A and C was stereoselectively accomplished by conformation-controlled substitution of allylic picolinate with Me2CuMgBr×MgBr2/ZnI 2. On the other hand, cyclobakuchiol B was synthesized by stereoselective addition of the cyclohexanecarboxylate enolate to CH 2/CHSOPh (see scheme). Copyright