Total Synthesis of (−)‐13‐Oxyingenol and its Natural Derivative

The use of photochemical transformations is a powerful strategy that allows for the formation of a high degree of molecular complexity from relatively simple building blocks in a single step. A central feature of all light-promoted transformations is the involvement of electronically excited states, generated upon absorption of photons. This produces transient reactive intermediates and significantly alters the reactivity of a chemical compound. The input of energy provided by light thus offers a means to produce strained and unique target compounds that cannot be assembled using thermal protocols. This review aims at highlighting photochemical transformations as a tool for rapidly accessing structurally and stereochemically diverse scaffolds. Synthetic designs based on photochemical transformations have the potential to afford complex polycyclic carbon skeletons with impressive efficiency, which are of high value in total synthesis.

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“… 238 − 250 In light of these challenges, a number of total syntheses of ingenol ( 2 ) have been reported. 38 , 251 − 261 …”

Section: [2 + 2] Photocycloadditionsmentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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“…The total synthesis of ingenane alcohol has been achieved, but the process is complex (over 14 steps) and produces low yields ( ca. 1%) [16-18]. In the present study, a simple and direct method was established to obtain ingenane alcohols from the E. kansui extract via a one-step deacylation as depicted in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui

Liu

Huang

et al. 2018

European Journal of Medicinal Chemistry

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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.

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“…In the present study, we address the possible antiviral activity of the labdane-type diterpene myriadenolide (12 S , 16-dihydroxy-ent-labda-7, 13-dien-15, 16-olide) for HTLV-1. The antiviral activity of the terpenes has been reported for HIV [ 27 , 28 ] and herpesvirus [ 29 ], among other viruses.…”

Section: Discussionmentioning

confidence: 99%

A reduction of viral mRNA, proteins and induction of altered morphogenesis reveals the anti-HTLV-1 activity of the labdane-diterpene myriadenolide in vitro

et al. 2014

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BackgroundHuman T-lymphotropic virus 1 (HTLV-1) has been associated with leukemia/lymphoma (ATL) and myelopathy/tropical spastic paraparesis (HAM/TSP), in addition to other inflammatory diseases as well as infection complications. Therapeutic approaches for HTLV-1-related pathologies are limited. The labdane diterpene myriadenolide (AMY) is a natural product that exhibit biological activities, such as anti-inflammatory and antiviral activity as reported for HIV and herpesvirus.ResultsWe demonstrated that this natural product was able to inhibit the expression of gag-pol mRNA and substantially reduced the expression of the structural proteins p19 and gp46. Comparison of treated and untreated cells shows that AMY alters both the morphology and the release of viral particles. The Atomic Force Microscopy assay showed that the AMY treatment reduced the number of particles on the cell surface by 47%.ConclusionWe demonstrated that the labdane diterpene myriadenolide reduced the expression of the structural proteins and the budding of viral particles, besides induces altered morphogenesis of HTLV-1, conferring on AMY a new antiviral activity that may be useful for the development of new compounds with specific anti-HTLV-1 activity.

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Total Synthesis of (−)‐13‐Oxyingenol and its Natural Derivative

Cited by 42 publications

References 28 publications

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui

A reduction of viral mRNA, proteins and induction of altered morphogenesis reveals the anti-HTLV-1 activity of the labdane-diterpene myriadenolide in vitro

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