54706-99-9Relevant articles and documents
On the active principles of the euphorbiaceae, IX. Ingenane type diterpene esters from five euphorbia species
Gotta,Adolf,Opferkuch,Hecker
, p. 683 - 694 (1984)
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Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui
Liu, Qingbo,Li, Wei,Huang, Li,Asada, Yoshihisa,Morris-Natschke, Susan L.,Chen, Chin-Ho,Lee, Kuo-Hsiung,Koike, Kazuo
supporting information, p. 618 - 627 (2018/07/29)
Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2.
Development of a concise synthesis of (+)-ingenol
McKerrall, Steven J.,J?rgensen, Lars,Kuttruff, Christian A.,Ungeheuer, Felix,Baran, Phil S.
, p. 5799 - 5810 (2014/05/06)
The complex diterpenoid (+)-ingenol possesses a uniquely challenging scaffold and constitutes the core of a recently approved anti-cancer drug. This full account details the development of a short synthesis of 1 that takes place in two separate phases (cyclase and oxidase) as loosely modeled after terpene biosynthesis. Initial model studies establishing the viability of a Pauson-Khand approach to building up the carbon framework are recounted. Extensive studies that led to the development of a 7-step cyclase phase to transform (+)-3-carene into a suitable tigliane-type core are also presented. A variety of competitive pinacol rearrangements and cyclization reactions were overcome to develop a 7-step oxidase phase producing (+)-ingenol. The pivotal pinacol rearrangement is further examined through DFT calculations, and implications for the biosynthesis of (+)-ingenol are discussed.
Total synthesis of ingenol
Nickel, Andrew,Maruyama, Toru,Tang, Haifeng,Murphy, Prescott D.,Greene, Blake,Yusuff, Naeem,Wood, John L.
, p. 16300 - 16301 (2007/10/03)
A total synthesis of the biologically important diterpene ingenol has been completed. Ring-closing olefin metathesis was used to construct the strained "inside-outside" tetracyclic skeleton, and a series of diastereoselective reactions were employed to complete the synthesis. Another naturally occurring ingenane, 20-deoxyingenol, has also been prepared. Copyright
