Total synthesis and absolute stereochemistry of plakortone E

Akiyama, Megumi; Isoda, Yuichi; Nishimoto, Masato; Narazaki, Maiko; Oka, Hiroaki; Kuboki, Atsuhito; Ohira, Susumu

doi:10.1016/j.tetlet.2006.02.025

Cited by 28 publications

(16 citation statements)

References 21 publications

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“…However, the absolute configurations of their stereocenters were not revealed in the initial structure elucidation 1. Recently, the absolute configurations of plakortones B,4d D,4a, b and E4c were established by total syntheses, but the absolute configurations of the other three plakortones (A, C, and F) still remain unknown…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Plakortone B

Xie¹,

Wu²,

Lee³

et al. 2010

Chemistry A European J

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Plakortone B is a naturally occurring bicyclic[3.3.0]furanolactone compound with attractive bioactivities. Although the relative configuration of plakortone B's central core had been established by NMR spectroscopic methods, the absolute configuration of its four stereocenters remained unknown. In the present paper, all four possible isomers of plakortone B were synthesized and one of these molecules was found to be identical with the natural plakortone B on the basis of (1)H, (13)C NMR spectra and specific rotation comparisons. Thus, the absolute configuration of the natural plakortone B was determined to be (3S,4S,6R,10R).

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of Plakortone B

Xie¹,

Wu²,

Lee³

et al. 2010

Chemistry A European J

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“…In an attempt to determine the correct stereochemistry of plakortone E, Ohira's group synthesized the natural product from the racemic diol 148 . The synthesized material, however, turned out to be (±)‐8‐ epi ‐plakortone E (147) (Scheme ) . The diol 148 was elaborated to the diol ether 149 via known procedure .…”

Section: Total Synthesis Of Furo[32‐b]furanone Natural Productsmentioning

confidence: 99%

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

et al. 2020

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The ubiquitous presence of highly oxygenated furo[3,2‐b]furanone fragments in diverse natural products with wide range of biological activities such as anti‐cancer, anti‐HIV, anti‐microbial activities, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Enticed by their potent biological activities and challenging polycyclic architecture, total synthesis of furo[3,2‐b]furanone natural products has witnessed intense activity in recent years with many notable achievements in the synthesis of structurally embellished family of bioactive metabolites such as plakortones, lactonamycines, schisanartanes, etc. While presenting a comprehensive account of post‐2000 syntheses of these natural products, through strategic and nuanced use of modern tools of organic synthesis, this review also aims to stimulate interest in exploring the diversity space around these natural products for newer applications.

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“…Polyketides with lactone fragment, i.e., plakortones A-G, are the second most prominent metabolites in these sponge-derived polyketides, exhibiting cardiac SR-Ca 2+ -pumping ATPase activating and in vitro cytotoxic activities [7,8,9]. The intrigoing structures and broad spectrum of bioactivities of the metabolites attracted attention on the chemical synthesis of such a cluster of molecules [21,22,23,24,25,26,27,28,29]. Also, the high flexibility of aliphatic chains or rings of these polyketides leads to a challenge in the absolute configuration identification.…”

Section: Introductionmentioning

confidence: 99%

“…Also, the high flexibility of aliphatic chains or rings of these polyketides leads to a challenge in the absolute configuration identification. The absolute configurations were determined at an early stage mainly by chemical methods, such as chemical degradation [30] and total synthesis [29,31,32]. In recent years, the calculating of NMR parameters provided a strong and convenient approach for the assignment of relative or absolute configuration of these highly flexible systems [33,34,35].…”

Section: Introductionmentioning

confidence: 99%

Chemistry and Selective Tumor Cell Growth Inhibitory Activity of Polyketides from the South China Sea Sponge Plakortis sp.

Cui

Riccio

et al. 2017

Marine Drugs

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Simplextone E (1), a new metabolite of polyketide origin, was isolated with eight known analogues (2–9) from the South China Sea sponge Plakortis sp. The relative configuration of the new compound was elucidated by a detailed analysis of the spectroscopic data and quantum mechanical calculation of NMR chemical shifts, aided by the newly reported DP4+ approach. Its absolute configuration was determined by the TDDFT/ECD calculation. Simplextone E (1) is proven to be one of the isomers of simplextone D. The absolute configuration at C-8 in alkyl chain of plakortone Q (2) was also assigned based on the NMR calculation. In the preliminary in vitro bioassay, compounds 6 and 7 showed a selective growth inhibitory activity against HCT-116 human colon cancer cells with IC50 values of 8.3 ± 2.4 and 8.4 ± 2.3 μM, corresponding to that of the positive control, adriamycin (IC50 4.1 μM). The two compounds also showed selective activities towards MCF-7 human breast cancer and K562 human erythroleukemia cells while compound 3 only displayed weak activity against K562 cells.

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Total synthesis and absolute stereochemistry of plakortone E

Cited by 28 publications

References 21 publications

Total Synthesis of Plakortone B

Total Synthesis of Plakortone B

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

Chemistry and Selective Tumor Cell Growth Inhibitory Activity of Polyketides from the South China Sea Sponge Plakortis sp.

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