Enantioselective Total Synthesis of (+)‐Flavisiamine F via Late‐Stage Visible‐Light‐Induced Photochemical Cyclization

Tong, Xiaogang; Shi, Bingfei; Liang, Kangjiang; Qian, Liu; Xia, Chengfeng

doi:10.1002/anie.201901241

Cited by 29 publications

(19 citation statements)

References 65 publications

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“…Xia and co‐workers reported first enantioselective total synthesis of (+)‐flavisiamine F 427 (Scheme 59), a kopsia alkaloid with caged and strained polycyclic skeleton, extracted from leaves of Kopsia flavida [240] . In this particular synthetic stratagem, an RCM was employed to construct the pentacyclic amine, shown in the Scheme 59.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

“…Xia and co-workers reported first enantioselective total synthesis of (+)-flavisiamine F 427 (Scheme 59), a kopsia alkaloid with caged and strained polycyclic skeleton, extracted from leaves of Kopsia flavida. [240] In this particular synthetic stratagem, an RCM was employed to construct the pentacyclic amine, shown in the Scheme 59. Methylation of homoallylic hydroxy group by converting it into the methyl ether with MeI/ Ag 2 O followed by the conversion of acetonyl moiety to tbutyldimethysilyl protected enol ether then deprotection of trichloroacetyl group with DIBALÀ H and subsequent alkylation of amine with allyl bromide/K 2 CO 3 afforded a secondary amine 424.…”

Section: Total Synthesis Of Natural Products Based On Rcmmentioning

confidence: 99%

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Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Section: Total Synthesis Of Natural Products Based On Rcmmentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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“…In view of the fact that the α-substituted cyclic carbonyl compounds can form chiral fixed all-carbon quaternary stereocenter by α-arylation, such as compounds 19a-19i, 26a-26g, and 29, which can effectively avoid the racemization of α-aryl compounds and subsequent reduce of optical purity. Moreover, the construction of chiral all-carbon quaternary stereocenter has always been attracted a majority of interests from the field of organic chemistry [52][53][54][55][56][57][58], so it is of great significance to design suitable substrates for such reactions. Hartwig et al initiated the asymmetric α-arylation of α-fluoroketone 34a under various catalytic systems.…”

Section: Palladium-catalyzed Intramolecular α-C(sp 3 )-H Arylations Of Cyclic Carbonyl Compoundsmentioning

confidence: 99%

α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds

Wang

et al. 2021

Nat. Prod. Bioprospect.

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Abstractα-C(sp3)-H arylation is an important type of C-H functionalization. Various biologically significant natural products, chemical intermediates, and drugs have been effectively prepared via C-H functionalization. Cyclic carbonyl compounds comprise of cyclic ketones, enones, lactones, and lactams. The α-C(sp3)-H arylation of these compounds have been exhibited high efficiency in forming C(sp3)-C(sp2) bonds, played a crucial role in organic synthesis, and attracted majority of interests from organic and medicinal communities. This review focused on the most significant advances including methods, mechanism, and applications in total synthesis of natural products in the field of α-C(sp3)-H arylations of cyclic carbonyl compounds in recent years.

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“…In 2019, Xia and co-workers reported the enantioselective total synthesis of (+)-flavisiamine (75) via a visiblelight-induced photoredox cyclization at a late stage (Scheme 12). 22 This synthesis began with the preparation of the free-radical precursor 72, which was prepared in 8 steps from carbazolone 71. The phenylsulfonyl protecting group was carefully chosen to facilitate photoredox cyclization by serving as a good radical leaving group and afford an imine that could be further transformed.…”

Section: Short Review Synthesismentioning

confidence: 99%

Visible-Light-Mediated Photoredox Reactions in the Total Synthesis of Natural Products

Mateus-Ruiz

Cordero‐Vargas²

2020

Synthesis

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In the last two decades, the field of photoredox catalysis (PRC) has grown impressively with reports of new synthetic methodologies and more efficient versions of known free-radical reactions. The impressive success of visible-light-mediated photoredox catalysis is, in great part, due to its low environmental impact, mild reaction conditions, clean reactions, and inexpensive methodologies. These features have allowed photoredox catalysis to emerge as a powerful tool in the synthesis of natural products; much excellent work was reported between 2011 and 2015. Since 2016, a number of more efficient and impressive total syntheses of natural products featuring photoredox catalysis have been reported. In this review, we summarize the recent synthetic applications of photoredox catalysis in the total synthesis of natural products between 2016 and 2020.1 Introduction2 Intermolecular Additions from Functionalized Substrates2.1 Intermolecular Additions from Alkyl Halides2.2 Intermolecular Additions from Alcohols and Carboxylic Acids3 Cyclizations from Functionalized Substrates3.1 Cyclizations of Carbon-Centered Radicals3.2 Cyclizations of Nitrogen-Centered Radicals4 Intramolecular Cyclization from Non-functionalized N–H Bonds4.1 Type I Radical Cascade4.2 Type II Radical Cascade4.3 Type III Radical Cascade5 Functionalization of Imines and Enamines6 Cycloadditions7 Miscellaneous7.1 Dehalogenation and Reductive Decarboxylation7.2 Thiyl Radical Promoted Cascade8 Conclusions and Perspectives

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Enantioselective Total Synthesis of (+)‐Flavisiamine F via Late‐Stage Visible‐Light‐Induced Photochemical Cyclization

Cited by 29 publications

References 65 publications

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Metathesis Reactions in Natural Product Fragments and Total Syntheses

α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds

Visible-Light-Mediated Photoredox Reactions in the Total Synthesis of Natural Products

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