Enantioselective and Collective Syntheses of Xanthanolides Involving a Controllable Dyotropic Rearrangement of <i>cis</i>‐β‐Lactones

Ren, Weiwu; Bian, Yichao; Zhang, Ziyang; Shang, Hai; Zhang, Pengtao; Chen, Yuejie; Yang, Zhen; Luo, Tuoping; Tang, Yefeng

doi:10.1002/anie.201202643

Cited by 55 publications

(30 citation statements)

References 49 publications

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“…The known compounds, 2-desoxy-6-epi-parthemollin (11), 14 xanthatin (12), 3b xanthinosin (13), 3b 11α,13-dihydro-4H-xanthalongin (14), 15 11α,13-dihydroxanthatin (15), 16 2-deacetyl-11β,13-dihydroxyxanthinin (16), 17 hydroxylindestenolide (17), 18 11β-13-dihydroxanthatin (18), 19 linderanlide C (19), 20 dihydrophaseic acid (20), 21 phaseic acid (21), 22 dihydrodiconiferyl alcohol (22), 23 threo-guaiacylglycerol-8′-vanillic acid ether (23), 24 caffeic acid ethyl ester (24), 25 and Figure S1, Supporting Information), were isolated and identified by comparing their experimental physical and spectroscopic data with literature values. Nitric oxide (NO) plays an important role in the inflammatory process, and an inhibitor of NO production may be considered as a potential anti-inflammatory agent.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum

Shi

Liu

et al. 2015

J. Nat. Prod.

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Seven new sesquiterpenes (1, 3-8), a new sesquiterpene natural product (2), and two new lignans (9 and 10), together with 15 known compounds, were isolated from the fruits of Xanthium sibiricum. The structures of the new compounds were established by NMR spectroscopic analysis, ECD calculations, and Mo2(OAc)4-induced circular dichroism, with the structures of 1 and 4 confirmed by single-crystal X-ray diffraction. Compound 1 is the first example of a 3/5/6/5 tetracyclic eudesmane sesquiterpene lactone formed at C-6 and C-7. In turn, compound 4 is the first example of a natural xanthane tetranorsesquiterpene, while compounds 5-8 are the first xanthane trinorsesquiterpenes found to date. Compounds 8, 11-15, 17, and 24 exhibited indirect anti-inflammatory activity by suppressing the lipopolysaccharide-induced proinflammatory factors in BV2 microglial cells, with IC50 values between 1.6 and 8.5 μM. Furthermore, compounds 13 and 17 exhibited anti-inflammatory activity against ear edema in mice produced by croton oil, with inhibition rates of 46.9% and 37.7%, respectively. Compounds 8, 11, 12, 23, and 24 exhibited potent activity against influenza A virus (A/FM/1/47, H1N1) with IC50 values between 3.7 and 8.4 μM.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum

Shi

Liu

et al. 2015

J. Nat. Prod.

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“…Recently, we achieved the collective synthesis of various monomeric xanthanolides with a dyotropic rearrangement of the 3,4‐ cis‐ β‐lactone as a key step 6. The chemistry paves the way for the synthesis of some more challenging targets such as 3 – 7 .…”

Section: Methodsmentioning

confidence: 99%

Biomimetic Synthesis: Discovery of Xanthanolide Dimers

et al. 2014

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Starting from xanthatin, the biomimetic synthesis of 4β,5β-epoxyxanthatin-1α,4α-endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head-to-head or head-to-tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and two of them, mogolides A and B, proved to be natural products present in the Xanthium mogolium Kitag plant.

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“…In 2012, Tang and co‐workers reported the total or formal syntheses of a series of 5/7‐ trans ‐fused xanthanolides . The key to their success hinged on a Wagner–Meerwein‐type dyotropic rearrangement of 3,4‐ cis ‐β‐lactones, which enabled access to the 5/7‐ trans bicyclic core of xanthanolides with excellent enantioselectivity and diastereoselectivity.…”

Section: Syntheses Of Monomeric Xanthanolidesmentioning

confidence: 99%

“…In 2012, Tang and co‐workers reported the collective synthesis of a series of 5/7‐ cis ‐xanthanolides from bicycle 32 , obtained through dyotropic rearrangement . As discussed above, 32 has been employed as a key intermediate to access various 5/7‐ trans ‐xanthanolides (Scheme ).…”

Section: Syntheses Of Monomeric Xanthanolidesmentioning

confidence: 99%

Advances in the Total Synthesis of Xanthanolide‐Type Sesquiterpenoids

Lei

Feng

Liu

et al. 2019

Chemistry An Asian Journal

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Xanthanolide-type sesquiterpenoids are ad iverse family of natural products isolated primarily from the genus Xanthium (Compositae). The intriguing molecular architectures and biological profileso ft hese natural products have rendered them attractive targets for total synthesis. This focus review aims to provide an up-to-date summary of progress in the chemical synthesis of xanthanolide-type ses-quiterpenoids. Different synthetic strategies to form 5/7-cisand 5/7-trans-bicyclic xanthanolides are presented in chronological order,w ith an emphasis on the key elements used to forge the characteristic 5/7-bicyclic cores of the targets. Recent advances in the total syntheses of structurally more complicated polycyclica nd dimeric xanthanolides are also discussed.The ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

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Enantioselective and Collective Syntheses of Xanthanolides Involving a Controllable Dyotropic Rearrangement of cis‐β‐Lactones

Cited by 55 publications

References 49 publications

Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum

Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum

Biomimetic Synthesis: Discovery of Xanthanolide Dimers

Advances in the Total Synthesis of Xanthanolide‐Type Sesquiterpenoids

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