Total Synthesis of (±)-Prostratin

Tong, Guanghu; Li, Zhi; Li, Pengfei

doi:10.1016/j.chempr.2018.10.002

Cited by 46 publications

(17 citation statements)

References 82 publications

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“…Prostratin (12-deoxyphorbol-13-acetate) is a 12-deoxytigliane diterpenoid, which acts as a protein kinase C activator and is potentially used to treat latent human immunodeficiency virus. The challenge of its semi synthesis and total chemical synthesis have been of great interest to chemists in recent years (Tong et al 2018 ). Although its mechanism of action has not been completely investigated, prostratin has been advanced into preclinical trials (Wang et al 2006 ).…”

Section: Introductionmentioning

confidence: 99%

Three new ent-abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell lines

Zhou

et al. 2019

Arch. Pharm. Res.

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Three new ent -abietane diterpenoids, termed fischerianoids A–C ( 1 – 3 ), were isolated and identified from the ethyl acetate extracts of roots of the medicinally valuable plant Euphorbia fischeriana . The planar and relative structures of 1 – 3 were established via high-resolution electrospray ionisation mass spectrometry and one- and two-dimensional nuclear magnetic resonance spectroscopic analyses, and the absolute configuration of 1 was further established via X-ray crystallography experiment. Compounds 1 – 3 showed selective inhibitory potency against certain human tumor cell lines with IC 50 values ranging from 8.50 ± 0.13 to 35.52 ± 0.08 μM. Graphical abstract Electronic supplementary material The online version of this article (10.1007/s12272-019-01151-y) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Three new ent-abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell lines

Zhou

et al. 2019

Arch. Pharm. Res.

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“…These 1,1-diaryl compounds are important pharmacophores, and their stereocontrolled preparation have been challenging through traditional protocols [62][63][64][65] . In our previous work, the cis-diol 19, a key intermediate of carbocyclic nucleosides 66 , was successfully employed for total synthesis of prostratin, a potent anti-HIV and antitumor natural product 67 . The trans-diol 22 is also an important synthetic intermediate of carbocyclic analogs of the antiviral ribavirin 68 .…”

Section: Resultsmentioning

confidence: 99%

A unified approach for divergent synthesis of contiguous stereodiads employing a small boronyl group

Zhan

Ding

et al. 2020

Nat Commun

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Acyclic contiguous stereocenters are frequently seen in biologically active natural and synthetic molecules. Although various synthetic methods have been reported, predictable and unified approaches to all possible stereoisomers are rare, particularly for those containing non-reactive hydrocarbon substituents. Herein, a β-boronyl group is employed as a readily accessible handle for predictable α-functionalization of enolates with either syn or anti selectivity depending on reaction conditions. Contiguous tertiary-tertiary and tertiaryquaternary stereocenters are thus accessed in generally good yields and diastereoselectivity. Based on experimental and computational studies, mechanism for syn selective alkylation is proposed, and Bpin (pinacolatoboronyl) behaves as a smaller group than most carboncentered groups. The synthetic utility of this methodology is demonstrated by preparation of several key intermediates for bioactive molecules.

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“…A stereoselective addition of vinylmagnesium bromide to tricyclic compound 345 directed the formation of a diene 346 , which effectively underwent RCM in presence of HG‐II catalyst 5 and produced a tetracyclic compound 347 which after several steps delivered the desired lancifodilactone G acetate. In stark contrast, Li and co‐workers revealed the total synthesis of (±)‐prostratin 352 (Scheme 45), a tigliane diterpene with protein kinase C (PKC) activation activity including RCM as crucial step [226] . The Ley's oxidation of secondary hydroxy group of compound 349 with tetrapropylammonium perruthenate (TPAP)/ N ‐Methylmorpholine N ‐oxide (NMO) and subsequent nucleophilic addition of 2‐methylallylzinc chloride directed the formation of a diene 350 .…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Total Synthesis of (±)-Prostratin

Cited by 46 publications

References 82 publications

Three new ent-abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell lines

Three new ent-abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell lines

A unified approach for divergent synthesis of contiguous stereodiads employing a small boronyl group

Metathesis Reactions in Natural Product Fragments and Total Syntheses

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