Total Synthesis of Mulberry Diels–Alder-Type Adducts Kuwanons G and H

Luo, Siyuan; Tang, Zhuo-Ya; Li, Qingjiang; Weng, Jiang; Yin, Sheng

doi:10.1021/acs.joc.1c00229

Cited by 17 publications

(31 citation statements)

References 23 publications

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“…Although the total synthesis of natural compounds is not covered in the present review, many of the procedures described have been utilized to prepare natural DA adducts and analogs. [128][129][130][131][132][133][134][135][136]…”

Section: Chalcones As Dienophilesmentioning

confidence: 99%

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mastachi-Loza

Ramírez-Candelero²,

Benítez‐Puebla

et al. 2022

Chemistry An Asian Journal

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Chalcones are aromatic ketones found in nature as the central core of many biological compounds. They have a wide range of biological activity and are biogenetic precursors of other important molecules such as flavonoids. Their pharmacological relevance makes them a privileged scaffold, advantageous for seeking alternative therapies in medicinal chemistry. Due to their structural diversity and ease of synthesis, they are often employed as building blocks for chemical transformations. Chalcones have a carbonyl conjugated system with two electrophilic centers that are commonly used for nucleophilic additions, as described in numerous articles. They can also participate in Diels-Alder reactions, which are [4 + 2] cycloadditions between a diene and a dienophile. This microreview presents a chronological survey of studies on chalcones as dienes and dienophiles in Diels-Alder cycloadditions. Although these reactions occur in nature, isolation of chalcones from plants yields very small quantities. Contrarily, synthesis leads to large quantities at a low cost. Hence, novel methodologies have been developed for [4 + 2] cycloadditions, with chalcones serving as a 2π or 4π electron system.

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Section: Chalcones As Dienophilesmentioning

confidence: 99%

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mastachi-Loza

Ramírez-Candelero²,

Benítez‐Puebla

et al. 2022

Chemistry An Asian Journal

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“…In 2021, the Tang group reported a convergent route towards the total synthesis of two MDAAs named kuwanons G and H (92 and 93) with unique dehydroprenylflavone dienes. The key features of this approach included the use of Baker-Venkataraman rearrangement, alkylation of β-diketone, intramolecular cyclization, and Suzuki-Miyaura coupling to achieve the unstable dehydroprenylflavone diene [194].…”

Section: Total Syntheses Of Kuwanons G and Hmentioning

confidence: 99%

Mulberry Diels–Alder-type adducts: isolation, structure, bioactivity, and synthesis

Luo

Zhu

Zou

et al. 2022

Nat. Prod. Bioprospect.

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Mulberry Diels–Alder-type adducts (MDAAs) are unique phenolic natural products biosynthetically derived from the intermolecular [4 + 2]-cycloaddition of dienophiles (mainly chalcones) and dehydroprenylphenol dienes, which are exclusively distributed in moraceous plants. A total of 166 MDAAs with diverse skeletons have been isolated and identified since 1980. Structurally, the classic MDAAs characterized by the chalcone-skeleton dienophiles can be divided into eight groups (Types A − H), while others with non-chalcone dienophiles or some variations of classic MDAAs are non-classic MDAAs (Type I). These compounds have attracted significant attention of natural products and synthetic chemists due to their complex architectures, remarkable biological activities, and synthetic challenges. The present review provides a comprehensive summary of the structural properties, bioactivities, and syntheses of MDAAs. Cited references were collected between 1980 and 2021 from the SciFinder, Web of Science, and China National Knowledge Internet (CNKI). Graphical Abstract

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“…In 2021, Luo et al reported the total synthesis of kuwanons G and H ( 11 and 12 ), two DAAs derived from the condensation of a chalcone with a flavone diene, that differs only in the presence of a prenyl group in kuwanon H ( 12 ) [ 95 ]. According to the retrosynthetic plan reported in Figure 48 , kuwanons G and H ( 11 and 12 ) could be obtained from the demethylation of methoxy groups of heptamethyl ether precursors 144 or 145 , which, in turn, could be prepared from Diels–Alder cycloaddition of diene 29 with 2′-hydroxychalcones 24 or 86 as dienophiles.…”

Section: Total Synthesis Of Mulberry Daasmentioning

confidence: 99%

Synthesis, Biosynthesis, and Biological Activity of Diels–Alder Adducts from Morus Genus: An Update

et al. 2022

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The plants of the Moraceae family are producers of a great variety of polyphenolic natural products. Among these, the Diels–Alder type adducts (DAAs) are endowed with a unique cyclohexene scaffold, since they are biosynthesized from [4+2] cycloaddition of different polyphenolic precursors such as chalcones and dehydroprenyl polyphenols. To date, more than 150 DAAs have been isolated and characterized from Moraceous and related plants. The main source of DAAs is the mulberry root bark, also known as “Sang-Bai-Pi” in Traditional Chinese Medicine, but they have also been isolated from root bark, stem barks, roots, stems or twigs, leaves, and callus cultures of Moraceous and other related plants. Since 1980, many biological activities of DAAs have been identified, including anti-HIV, antimicrobial, anti-inflammatory, and anticancer ones. For these reasons, natural DAAs have been intensively investigated, and a lot of efforts have been made to study their biosynthesis and to establish practical synthetic access. In this review, we summarized all the updated knowledge on biosynthesis, chemoenzymatic synthesis, racemic and enantioselective total synthesis, and biological activity of natural DAAs from Moraceous and related plants.

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Total Synthesis of Mulberry Diels–Alder-Type Adducts Kuwanons G and H

Cited by 17 publications

References 23 publications

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mulberry Diels–Alder-type adducts: isolation, structure, bioactivity, and synthesis

Synthesis, Biosynthesis, and Biological Activity of Diels–Alder Adducts from Morus Genus: An Update

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