24909-95-3

Usage

Uses

Used in Pharmaceutical Industry:
(1'R,3R,7'aβ)-1'β,7'α-Dihydroxy-3'aβ,4'β-dimethyl-4-methylenespiro[oxolane-3,2'-hydrindane]-2-one is used as a potential pharmaceutical candidate due to its unique structural features and functional groups. The presence of hydroxyl, methyl, and methylene groups, along with the hydrindane core, may contribute to its biological activity or pharmacological properties, making it a compound of interest for further research and development in drug discovery and design.

Upstream product

• 322479-99-2 C₁₅H₂₀O₄ 
• 322480-03-5 C₁₅H₁₈O₄ 
• 322480-02-4 (+)-1,10-didehydro-7-epi-9α-hydroxy-bakkenolide A 
• 192197-74-3 (2'S,3a'R,4'S,7a'S)-3a',4'-dimethyl-4-methyleneoctahydro-2H-spiro[furan-3,2'-indene]-1',2-(3'H)-dione 
• 322479-98-1 (-)-1,10-didehydro-7-epi-9-oxo-bakkenolide A 
• 192197-73-2 (1S,2R,6S,8S)-ethyl-1,2-dimethyl-7-oxobicyclo[4.3.0]nonane-8-carboxylate 
• 122518-91-6 (S)-1,6-dimethyl-1-cyclohexene 
• 122452-76-0 Phenyl-carbamic acid (R)-2-methyl-cyclohex-2-enyl ester 
• 122518-90-5 (1R,2S,6S)-8,8-Dichloro-1,2-dimethyl-bicyclo[4.2.0]octan-7-one 
• 6610-16-8 (R)-(+)-2-methyl-2-cyclohexen-1-ol 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 322480-00-2 (2S,3aR,4S,7aS)-prop-2-ynyl 3a,4-dimethyl-1-oxooctahydro-1H-indene-2-carboxylate 
• 950488-18-3 (+)-1α-hydroxy-7-epi-9-oxo-bakkenolide A 
• 950488-17-2 (+)-1α-{[(tert-butyl)dimethylsilyl]oxy}-7-epi-9-oxo-bakkenolide A 

Downstream Products

• 19903-94-7 (-)-bakkenolide L 
• 18455-98-6 bakkenolide B 
• 18456-00-3 (-)-Bakkenolide C 

Relevant academic research and scientific papers

Enantiospecific total synthesis of (-)-bakkenolide III and formal total synthesis of (-)-bakkenolides B, C, H, L, V, and X

A concise enantiospecific synthesis of (-)-bakkenolide III was accomplished from (S)-(+)-carvone. The key step involved radical cyclization of an iodoketone intermediate which afforded the cis-hydrindanone skeleton. Further synthetic transformations generated bakkenolide III, which also constitutes the formal total synthesis of (-)-bakkenolides, B, C, H, L, V, and X.

First comprehensive bakkane approach: Stereoselective and efficient dichloroketene-based total syntheses of (±)- and (-)-9-acetoxyfukinanolide, (±)- and (+)-bakkenolide a, (-)-bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-homogynolide A, (±)-homogynolide B, and (±)-palmosalide C

Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro β-methylene-γ-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.

The first entry to complex bakkanes: A highly effective retroaldol-aldol-based approach to (-)-bakkenolides III B, C, and H

A novel SmI2-promoted chemoselective double reduction of an epoxy ketone and a thermodynamically governed retroaldol-aldol reaction have allowed the first successful entry to enantio-pure (-)-bekkenolide III (1) to be realized. This compound ha