Spirolindemers A and B, Lindenane Sesquiterpenoid Oligomers Equipped with Oxaspiro[4.5]decane from <i>Chloranthus henryi</i>

Li, Jixin; Chi, Jun; Tang, Pengfei; Sun, Yunpeng; Lu, Wei-Jia; Xu, Wen-Jun; Wang, Yongyue; Luo, Jun; Kong, Ling–Yi

doi:10.1002/cjoc.202100743

Cited by 28 publications

(19 citation statements)

References 24 publications

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“…More and more chimeric natural products have been identified, and most of them showed significant bioactivities. [ 35‐36 ] Herein, this ingenious reaction provides an effective method for the synthesis of asymmetric methylene‐bridged dimers. Moreover, some common natural products, such as 4‐hydroxycoumarin ( 25 ) and SEK34b ( 26 ), can also be used efficiently during that process.…”

Section: Resultsmentioning

confidence: 99%

Discovery of New Bohemamines and Synthesis of Methylene‐Bridged Chimeric Derivatives through Natural Product Chimera Strategy

et al. 2022

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Five new pyrrolizidine alkaloids, bohemamines J-N (1-5), were isolated from Streptomyces sp. CPCC 200497. Their structures were assigned based on detailed spectroscopic analysis and semisynthesis. Bohemamine J (1) possesses a new chimeric skeleton derived from bohemamine A (6) and phenylacetaldehyde. Inspired by the nonenzymatic formation mechanism of the methylene-bridged dimers isolated from this strain, we synthesized a series of chimeric derivatives (8, 9, and 12-23) through natural product chimera strategy. Compounds 13, 15, 19, and 21 showed significant antioxidant activity.

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Section: Resultsmentioning

confidence: 99%

Discovery of New Bohemamines and Synthesis of Methylene‐Bridged Chimeric Derivatives through Natural Product Chimera Strategy

et al. 2022

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“…11−13 In lindenane polymers, the cyclopropane is usually accompanied by Δ 4 , which makes it susceptible to various reactions, such as vinylcyclopropane rearrangement 14−16 and cyclopropylcarbonyl rearrangement, resulting in a 5/6-fused fragment 17 and a 5/ 3/6 carbon fragment. 18,19 In our previous studies, trimers obtained by acetalization, esterification, 9 or hetero-Diels− Alder additions 10 have been isolated from Chloranthaceae plants. Thus, the potential for rearranged lindenane polymers with novel skeletons or linkage remains enormous, which also attracts our attention.…”

Section: ■ Introductionmentioning

confidence: 99%

Rearranged Lindenane Sesquiterpenoid Trimers from Chloranthus fortunei: Target Discovery and Biomimetic Conversion

Wang

Sun

et al. 2022

J. Org. Chem.

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Seven lindenane-type sesquiterpenoid trimers, including four new ones (1−4) and three known analogues (5− 7), were isolated from Chloranthus fortunei guided by highperformance liquid chromatography with photodiode array detection with characteristic absorption at 210 and 350 nm. Their structures, including absolute configurations, were achieved by high-resolution mass spectrometry, nuclear magnetic resonance, electronic circular dichroism, and quantum chemical calculations. Compound 1 was the first example of two lindenane units connected by a C-15−C-15′ bond. The 5/7/5-fused ring system in 2 was presumably formed biogenetically by key keto−enol tautomerism and Cope rearrangement from 5. The 5/3/6 carbon skeleton in 3−5 and epi-cyclopropane in 3 and 6 might have originated from trishizukaol A (7) with a normal 3/5/6-fused ring system through vinylcyclopropane rearrangement. The biomimetic conversion from 7 to 3−6 was successfully achieved by adding a 365 nm ultraviolet lamp and a free radical initiator, and 2 was also spontaneously converted to 5 in methanol and CDCl 3 , which proved the correctness of the structural identification and the speculation described above. Compounds 1−7 exhibited antiinflammatory activity with IC 50 values in the range of 2.90−22.80 μmol/L.

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“…Spirocyclic compounds are a distinctive class of compounds, which have drawn continuous attention due to antiviral, antitumor, antibacterial, and antioxidant activities . Among spirocarbocycles, spiro[5.5]enones and spiro[4.5]enones act as the key fundamental frameworks and are present in numerous natural products and biologically active molecules .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Spiro[5.5]trienones- and Spiro[4.5]trienones-Fused Selenocyanates via Electrophilic Selenocyanogen Cyclization and Dearomative Spirocyclization

Wang

Yang

et al. 2022

J. Org. Chem.

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A practical strategy for the synthesis of spiro[5.5]trienones-fused selenocyanates and spiro[4.5]trienones-fused selenocyanates through electrophilic selenocyanogen cyclization and dearomative spirocyclization is reported. This approach was conducted under mild conditions with broad substrate scope and good functional group tolerance. The utility of this procedure is exhibited in the late-stage functionalization of nature product and drug molecules.

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Spirolindemers A and B, Lindenane Sesquiterpenoid Oligomers Equipped with Oxaspiro[4.5]decane from Chloranthus henryi

Cited by 28 publications

References 24 publications

Discovery of New Bohemamines and Synthesis of Methylene‐Bridged Chimeric Derivatives through Natural Product Chimera Strategy

Discovery of New Bohemamines and Synthesis of Methylene‐Bridged Chimeric Derivatives through Natural Product Chimera Strategy

Rearranged Lindenane Sesquiterpenoid Trimers from Chloranthus fortunei: Target Discovery and Biomimetic Conversion

Synthesis of Spiro[5.5]trienones- and Spiro[4.5]trienones-Fused Selenocyanates via Electrophilic Selenocyanogen Cyclization and Dearomative Spirocyclization

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