6-Methoxypodophyllotoxin-7-<i>O</i>-n-Hexanoate, a New Aryltetralin Lignan Ester from Seeds of<i>Linum flavum</i>

Klaes, Michael; Ellendorff, Therese; Schmidt, Thomas J.

doi:10.1055/s-0029-1240674

Cited by 9 publications

(3 citation statements)

References 9 publications

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“…In addition, a thermal retro-aldol reaction of 9 afforded isopicropodophyllone (15), which could be reduced to generate either epiisopicropodophyllotoxin (16) 52 or epiisopicrodeoxypodophyllotoxin (17). Using this new protocol from either 2k′ or 2l′, we also synthesized β-peltatin-A-methyether (18) and accomplished the rst total syntheses of epiisopicropodophyllotoxin (16), 6-methoxypodophyllotoxin (19), 6methoxypodophyllotoxin-7-O-n-hexanoate (20), 53 cleistantoxin (21), 54 and picrobursenin ( 22) 55 (Fig. 3b).…”

Section: Main Textmentioning

confidence: 99%

Cyclolignan Synthesis Streamlined by Enantioselective Hydrogenation of Tetrasubstituted Olefins

Xu,

Peng,

et al. 2024

Preprint

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All Birds with One Stone: Natural products have long been valuable sources of inspiration for drug discovery. Unfortunately, the inherent limitations of direct semisynthetic derivatizations have become more and more obvious, and the need to overcome these limitations is particularly urgent nowadays because the most valuable natural products tend to be isolated in minute amounts. Therefore, de novo synthesis with ideal modularity and diversity, have been a critical goal in drug discovery research. However, this endeavor of complex natural products is highly challenging, and only limited success has been achieved so far. Herein, we report a powerful, general platform for cyclolignan synthesis involving challenging rhodium-catalyzed enantioselective hydrogenation of tetrasubstituted 1,2-dihydronaphthalene esters (> 40 examples; up to 99% y, >99% ee). This unique platform allows ready access to various types of cyclolignans, as exemplified by the expedient and mostly protecting-group-free synthesis of over thirty cyclolignans, including many that have not previously been synthesized, such as 6-methoxy podophyllotoxin, cleistantoxin, picrobursenin, austrobailignan-4, aglacins D and F-H (with three revised structures), (+)-lirionol, ovafolinin D, and fimbricalyxoid A. We expect this work to inspire modular, de novo diversity-oriented syntheses of other important classes of natural products and thus to rejuvenate the role of natural products in drug discovery and development.

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Section: Main Textmentioning

confidence: 99%

Cyclolignan Synthesis Streamlined by Enantioselective Hydrogenation of Tetrasubstituted Olefins

Xu,

Peng,

et al. 2024

Preprint

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“…Introducing amino group into these molecules also made further modifications possible. A series of saturated aliphatic amide derivatives (111)(112)(113)(114)(115)(116)(117) were synthesized by linking 4β-amino-4-deoxypodophyllotoxin with succinic acid [141], among which, compounds 113-117 showed more potent antitumor activity than etoposide. More inspiringly, they could reverse MDR against K562/AO2 in vitro.…”

Section: Ring Cmentioning

confidence: 99%

Chemistry and Biological Activities of Naturally Occurring and Structurally Modified Podophyllotoxins

et al. 2022

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Plants containing podophyllotoxin and its analogues have been used as folk medicines for centuries. The characteristic chemical structures and strong biological activities of this class of compounds attracted attention worldwide. Currently, more than ninety natural podophyllotoxins were isolated, and structure modifications of these molecules were performed to afford a variety of derivatives, which offered optimized anti-tumor activity. This review summarized up to date reports on natural occurring podophyllotoxins and their sources, structural modification and biological activities. Special attention was paid to both structural modification and optimized antitumor activity. It was noteworthy that etoposide, a derivative of podophyllotoxin, could prevent cytokine storm caused by the recent SARS-CoV-2 viral infection.

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“…Klaes [ 46 ] isolated a new aryltetralin lignan from the seeds of L. flavum , var. compactum, previously detected in the aerial parts of several Linum species, and which has not been previously reported.…”

Section: Lignans From Plants Of Different Speciesmentioning

confidence: 99%

NMR Characterization of Lignans

Consonni¹,

Ottolina²

2022

Molecules

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Lignans are particularly interesting secondary metabolites belonging to the phenyl-propanoid biosynthetic pathway. From the structural point of view, these molecules could belong to the aryltetralin, arylnaphtalene, or dibenzylbutyrolactone molecular skeleton. Lignans are present in different tissues of plants but are mainly accumulated in seeds. Extracts from plant tissues could be characterized by using the NMR-based approach, which provides a profile of aromatic molecules and detailed structural information for their elucidation. In order to improve the production of these secondary metabolites, elicitors could effectively stimulate lignan production. Several plant species are considered in this review with a particular focus on Linum species, well recognized as the main producer of lignans.

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6-Methoxypodophyllotoxin-7-O-n-Hexanoate, a New Aryltetralin Lignan Ester from Seeds ofLinum flavum

Cited by 9 publications

References 9 publications

Cyclolignan Synthesis Streamlined by Enantioselective Hydrogenation of Tetrasubstituted Olefins

Cyclolignan Synthesis Streamlined by Enantioselective Hydrogenation of Tetrasubstituted Olefins

Chemistry and Biological Activities of Naturally Occurring and Structurally Modified Podophyllotoxins

NMR Characterization of Lignans

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