29444-03-9

Usage

Uses

Used in Pharmaceutical Industry:
Jatrophone is used as a pharmaceutical compound for its potential role in tumor growth inhibition. Its unique structure allows it to be readily attacked by nucleophiles, making it a promising candidate for the development of new drugs and therapies targeting cancer cells.
Used in Biochemical Research:
In the field of biochemical research, Jatrophone is utilized as a tool to study various aspects of cellular growth and regulation. Its interaction with nucleophiles and its effects on tumor growth make it a valuable asset for understanding the underlying mechanisms of cancer and other related diseases.
Used in Drug Development:
Jatrophone's properties also make it a potential candidate for drug development. Its unique structure and reactivity with nucleophiles can be harnessed to create new compounds with targeted effects on specific cellular processes, potentially leading to the development of more effective treatments for various diseases, including cancer.

InChI:InChI=1/C20H24O3/c1-12-8-15-9-13(2)16(21)6-7-19(4,5)11-17-14(3)18(22)20(15,10-12)23-17/h6-9,12H,10-11H2,1-5H3/b7-6-,13-9-

Upstream product

• 142843-52-5 Trifluoro-methanesulfonic acid (5R,8R)-2-(2,2-dimethyl-but-3-ynyl)-3,8-dimethyl-4-oxo-1-oxa-spiro[4.4]nona-2,6-dien-6-yl ester 
• 142843-64-9 (5R,8R)-6-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-2-(2,2-dimethyl-but-3-ynyl)-3,8-dimethyl-1-oxa-spiro[4.4]nona-2,6-dien-4-one 
• 142843-65-0 (Z)-(1R,3R)-8-Hydroxy-3,7,11,11,14-pentamethyl-16-oxa-tricyclo[11.2.1.0^1,5]hexadeca-4,6,13-trien-9-yn-15-one 
• 142843-63-8 (5R,8R)-2-(2,2-Dimethyl-but-3-ynyl)-6-((Z)-3-hydroxy-2-methyl-propenyl)-3,8-dimethyl-1-oxa-spiro[4.4]nona-2,6-dien-4-one 
• 142843-49-0 3,3-Dimethyl-pent-4-ynoyl chloride 
• 67099-40-5 3,3-dimethyl-4-pentynoic acid 
• 142843-66-1 (+)-8,9-dehydrojatrophone 
• 201230-82-2 carbon monoxide 
• 129873-10-5 Trifluoro-methanesulfonic acid (Z)-2-[(5R,8R)-2-((E)-2,2-dimethyl-4-tributylstannanyl-but-3-enyl)-3,8-dimethyl-4-oxo-1-oxa-spiro[4.4]nona-2,6-dien-6-yl]-1-methyl-vinyl ester 
• 129873-10-5 Trifluoro-methanesulfonic acid (Z)-2-[(5R,8S)-2-((E)-2,2-dimethyl-4-tributylstannanyl-but-3-enyl)-3,8-dimethyl-4-oxo-1-oxa-spiro[4.4]nona-2,6-dien-6-yl]-1-methyl-vinyl ester 
• 142926-26-9 (Z)-3-[(5R,8R)-2-(2,2-Dimethyl-but-3-ynyl)-3,8-dimethyl-4-oxo-1-oxa-spiro[4.4]nona-2,6-dien-6-yl]-2-methyl-propenal 
• 142843-50-3 3,3-Dimethyl-pent-4-ynoic acid (1R,4R)-1-[2-(diethoxy-phosphoryl)-propionyl]-4-methyl-2-trifluoromethanesulfonyloxy-cyclopent-2-enyl ester 

Downstream Products

• 1448443-63-7 C₂₇H₂₇F₃O₃ 
• 1448443-62-6 C₂₆H₂₈O₃ 
• 1448443-61-5 C₂₇H₃₀O₄ 

Relevant academic research and scientific papers

Total synthesis of (+)-jatrophone

The first total synthesis of optically active (+)-jatrophone is described. A convergent sequence provides the natural enantiomer in just 12 steps from (R)-(+)-3-methyladipic acid. Key steps include formation of the jatrophone C-ring through a Wadsworth-Horner-Emmons variant, a Pd-catalyzed cross-coupling that incorporates the C5-C6 double bond with the required Z-stereochemistry, and formation of the macrocycle by condensation of an acetylenic aldehyde. This sequence provides a short, efficient, and stereocontrolled route to the complex diterpenoid (+)-jatrophone.

Total synthesis of (±)-epi-jatrophone and (±)-jatrophone using palladium-catalyzed carbonylative coupling of vinyl triflates with vinylstannanes as the macrocycle-forming step

Jatrophone is a macrocyclic diterpene which exhibits significant inhibitory activity in vivo and in vitro against various carcinomas. The synthesis of (±)-jatrophone and its epimer was completed with use of a palladium-catalyzed carbonylative coupling of a vinylic triflate with an organostannane as the key step. The synthesis of epi-jatrophone was first completed to establish the chemistry for jatrophone. The overall sequence for each synthesis required 16 steps starting from 4-methyl-2-cyclopenten-1-one. The overall yields were 0.83% and 0.28%, respectively.