79720-52-8

Upstream product

• 30220-46-3 ingenol 
• 76-83-5 trityl chloride 
• 30220-45-2 ingenol 3,5,20-triacetate 
• 77573-44-5 ingenol-3,4:5,20-diacetonide 
• 77573-43-4 (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one 

Downstream Products

• 256427-34-6 ingenol 3-benzoate-20-trityl ether 
• 59086-90-7 Ingenol dibenzoate 
• 256427-36-8 20-deoxy-20-fluoroingenol 3,5-dibenzoate 
• 256427-40-4 20-chloro-20-deoxyingenol 3,5-dibenzoate 
• 77495-85-3 ingenol 3,5-dibenzoate 

Relevant academic research and scientific papers

A convenient method for the preparation of 20-[18O]-labeled ingenol

A short and efficient protecting group-free synthesis of isotopically labeled 20-[18O]-ingenol has been developed. Based on a highly selective (only one out of four hydroxy groups) Mitsunobu reaction of ingenol with 18O2-acetic acid and subsequent methanolysis, this route yielded the desired 20-[18O]-ingenol in high yield and chemical and isotopic purity.

Synthesis of modified ingenol esters

Synthetic protocols for the manipulation of the polyhydroxylated southern region of ingenol (1a) were developed, and a series of isosteres of the anticancer compound ingenol 3,20-dibenzoate (1b) was prepared. The biological evaluation of these compounds showed that cytotoxicity was relatively tolerant to changes at C-20, while PKC activation was markedly affected by these modifications. These data suggest that chemical manipulation can effectively dissect cytotoxicity and tumour-promoting activity (or potential) of ingenoids, affording more optimal candidates for development, like 20-deoxy-20-fluoroingenol 3,20-dibenzoate (5b). In mild acidic medium, an unexpected vinylogous retro-pinacol rearrangement of ingenol to a tigliane derivative was observed.

On the Chemistry of Ingenol, I. Ingenol and Some of its Derivatives

The tetracyclic polyfunctional diterpene ingenol (1) is the prototype of many diterpenoid parent alcohols of the ingenane type.Esters of these parent alcohols occur-partly together with esters of polyfunctional diterpene parent alcohols of the tigliane and daphnane type - as irritant, cocarcinogenic and antineoplastic principles in spesies of the family Euphorbiaceae (Spurge).Preparation of 1 from latex of Euphorbia ingens E.May as well as of some functional derivatives of 1 are described. - Key words: Cocarcinogens, Diterpene Esters, Euphorbiaceae, Tumor Promoters