Collective Total Syntheses of Atisane‐Type Diterpenes and Atisine‐Type Diterpenoid Alkaloids: (±)‐Spiramilactone B, (±)‐Spiraminol, (±)‐Dihydroajaconine, and (±)‐Spiramines C and D

Cheng, Hang; Zeng, Fanhao; Yang, Xue; Meng, Yin-Juan; Xu, Liang; Wang, Feng‐Peng

doi:10.1002/ange.201508996

Cited by 25 publications

(7 citation statements)

References 61 publications

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“…A nitrogen-containing compound called aurantiamide acetate has been found in an ethanolic extract of S. formosana branches [ 34 ]. Some alkaloids of spireas have been successfully synthesized artificially [ 123 ].…”

Section: Chemical Components and Biological Activity Of The Isolated Substancesmentioning

confidence: 99%

Phytoconstituents and Bioactivity of Plants of the Genus Spiraea L. (Rosaceae): A Review

Kostikova

Петрова

2021

IJMS

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The genus Spiraea L. belongs to the Rosaceae Juss. family and includes more than 100 species distributed in the temperate zone and subtropical zone of the Northern Hemisphere at the center of species diversity in East Asia. Representatives of the genus are known as ornamental plants with many forms and varieties, are widely used in conventional medicine, and have a high resource potential. This review provides information on the diversity of phenolic compounds (flavonoids, phenolcarboxylic acids, and lignans), terpenoids, alkaloids, steroids, and other classes of secondary metabolites in the species of Spiraea worldwide. The article also presents little-known and hard-to-find data published in Russian concerning Spiraea phytochemistry. The biological activities of extracts and their fractions and of individual compounds having different types of biological activity (e.g., antioxidant, antibacterial, anti-inflammatory, and antifungal) are discussed. Data about biotechnological research on representatives of the genus Spiraea are presented too. The analysis of the literature showed that further chemical and pharmacological studies on Spiraea plants are quite promising.

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Section: Chemical Components and Biological Activity Of The Isolated Substancesmentioning

confidence: 99%

Phytoconstituents and Bioactivity of Plants of the Genus Spiraea L. (Rosaceae): A Review

Kostikova

Петрова

2021

IJMS

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“…The short synthesis is truly impressive for such formidable and challenging targets. In 2017, the Martin group reported a unique approach to formal synthesis of the other two members of ETP alkaloids, T988C (145) and gliocladine C (146), and total synthesis of a related hexahydropyrrolo [2,3-b]indole diketopiperazine (DKP) alkaloid gliocladin C (144) from the common intermediate 141 (Scheme 14). 52 The synthesis of 141 features an unprecedented nucleophilic addition of a diketopiperazine to N-allyl isatin and a Friedel−Crafts alkylation of the resulting tertiary alcohol with indole to install the key quaternary center.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…In addition, 141 was converted into 142 and 143 through N-protection and regioselective hydration followed by subsequent protection, respectively. T988C (145) and gliocladine C (146) could be synthesized from 142 and 143 respectively by using the published procedures.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…Vinylogous Mannich reaction of 1021 and aminol 1022 using triisopropylsilyl triflate as the Lewis acid gave the desired adduct 1023. 145 The synthesis of the pivotal hexacyclic intermediate 1088 was achieved through a unique retro Diels−Alder/intramolecular Diels−Alder cascade sequence, which allowed rapid access to the tricyclo[6.2.2.0] ring system and a diastereoselective Rucatalyzed 1,7-enyne cycloisomerization to construct the highly functionalized tetracyclic atisane skeleton 1085. Dihydroajaconine (1090) could be obtained by reduction and condensation of 1088 followed by NaBH 4 reduction of 1089.…”

Section: The Other Natural Productsmentioning

confidence: 99%

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Divergent Strategy in Natural Product Total Synthesis

et al. 2018

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The divergent total syntheses of complex natural products from a common intermediate have attracted enormous attention in the chemical community in the past few years because it can improve the efficiency of chemical synthesis. A number of powerful and unified strategies have been developed by emulating the natural biosynthesis or through innovative transformations. This review focuses on the total synthesis of natural products by applying divergent strategies and the literature covering from 2013 to June 2017. On the basis of where the diversity comes from, the examples are grouped into three parts and discussed in detail. In each group, the examples that synthesize natural products belonging to the same subfamily are put together to contrast with one another.

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“…Over the past decade, the synthetic community has made great efforts in pursuit of the total synthesis of atisane diterpenes and their related diterpenoid alkaloids with some notable successes 2 3 4 19 20 21 22 23 24 25 26 27 28 . The teams of Carreira and Liu reported creative solutions for the total synthesis of a 3,4-seco atisane diterpene (crotogoudin, 7 , Fig.…”

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confidence: 99%

Total synthesis of atropurpuran

Gong¹,

Chen²,

Liu³

et al. 2016

Nat Commun

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Due to their architectural intricacy and biological significance, the synthesis of polycyclic diterpenes and their biogenetically related alkaloids have been the subject of considerable interest over the last few decades, with progress including the impressive synthesis of several elusive targets. Despite tremendous efforts, conquering the unique structural types of this large natural product family remains a long-term challenge. The arcutane diterpenes and related alkaloids, bearing a congested tetracyclo[5.3.3.04,9.04,12]tridecane unit, are included in these unsolved enigmas. Here we report a concise approach to the construction of the core structure of these molecules and the first total synthesis of (±)-atropurpuran. Pivotal features of the synthesis include an oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade, sequential aldol and ketyl-olefin cyclizations to assemble the highly caged framework, and a chemoselective and stereoselective reduction to install the requisite allylic hydroxyl group in the target molecule.

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Collective Total Syntheses of Atisane‐Type Diterpenes and Atisine‐Type Diterpenoid Alkaloids: (±)‐Spiramilactone B, (±)‐Spiraminol, (±)‐Dihydroajaconine, and (±)‐Spiramines C and D

Cited by 25 publications

References 61 publications

Phytoconstituents and Bioactivity of Plants of the Genus Spiraea L. (Rosaceae): A Review

Phytoconstituents and Bioactivity of Plants of the Genus Spiraea L. (Rosaceae): A Review

Divergent Strategy in Natural Product Total Synthesis

Total synthesis of atropurpuran

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