Total Synthesis of Four Classes of <i>Daphniphyllum</i> Alkaloids

Zhang, Wenhao; Lu, Ming; Ren, Lu; Zhang, Xiang; Liu, Shaonan; Ba, Mengyu; Yang, Peng; Li, Ang

doi:10.1021/jacs.3c06088

Cited by 14 publications

(8 citation statements)

References 84 publications

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“…Relying and ring-by-ring synthetic strategy, Li et al successfully completed the total synthesis of (+)-daphnicyclidin A (1), (À )-daphnicyclidin D (4), (À )-daphnicyclidin F ( 6) and (À )-daphnicyclidin K (10). [35] Riding a previously published route from their own lab, [36a,b] non-racemic 156 [33a,b,34] was subjected to Mitsunobu reaction to yield the propargylic amine 157 (Scheme 18). Since six-membered 156 is used as an A ring building block, a downstream one-carbon ring expansion is required.…”

Section: Synthetic Effortsmentioning

confidence: 99%

Daphnicyclidin Alkaloids 2001–2023

Gierok,

Hiersemann

2024

Eur J Org Chem

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The Daphniphyllum alkaloids represent a particularly diverse class of complex diterpene alkaloids, which are characterized by their enormous structural diversity. The daphnicyclidins, a subgroup of these alkaloids, stand out due to their unique pentafulvene structural motif. This review article gives an overview of the compounds that have been isolated so far and can be assigned to this subgroup. Furthermore, all synthesis approaches and total syntheses published to date are presented.

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Section: Synthetic Effortsmentioning

confidence: 99%

Daphnicyclidin Alkaloids 2001–2023

Gierok,

Hiersemann

2024

Eur J Org Chem

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“…In addition, it can also be utilized in the late stages of syntheses, thereby allowing the divergent syntheses of a collection of natural products with distinct but closely related scaffolds. 34–36…”

Section: Introductionmentioning

confidence: 99%

Controllable skeletal reorganizations in natural product synthesis

Zhang,

Qian,

et al. 2024

Nat. Prod. Rep.

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“…Inspired by the carbocationic cyclization/rearrangements in their biosynthetic pathways and in connection with our interest in the divergent synthesis, we envisaged that these related platensilin-type natural products could be forged through the C–C bond cyclization–cleavage protocols from a common ent -pimarene core A2 (Scheme ). This approach could further diversify into unnatural polycyclic frameworks, culminating in the synthesis of both these natural products and their skeletally diverse analogs.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis and Biological Evaluation of Platensilin, Platensimycin, Platencin, and Their Analogs via a Bioinspired Skeletal Reconstruction Approach

Gao,

Wang,

et al. 2024

J. Am. Chem. Soc.

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Platensilin, platensimycin, and platencin are potent inhibitors of β-ketoacyl−acyl carrier protein synthase (FabF) in the bacterial and mammalian fatty acid synthesis system, presenting promising drug leads for both antibacterial and antidiabetic therapies. Herein, a bioinspired skeleton reconstruction approach is reported, which enables the unified synthesis of these three natural FabF inhibitors and their skeletally diverse analogs, all stemming from a common ent-pimarane core. The synthesis features a diastereoselective biocatalytic reduction and an intermolecular Diels−Alder reaction to prepare the common ent-pimarane core. From this intermediate, stereoselective Mn-catalyzed hydrogen atom−transfer hydrogenation and subsequent Cu-catalyzed carbenoid C−H insertion afford platensilin. Furthermore, the intramolecular Diels−Alder reaction succeeded by regioselective ring opening of the newly formed cyclopropane enables the construction of the bicyclo[3.2.1]-octane and bicyclo[2.2.2]-octane ring systems of platensimycin and platencin, respectively. This skeletal reconstruction approach of the ent-pimarane core facilitates the preparation of analogs bearing different polycyclic scaffolds. Among these analogs, the previously unexplored cyclopropyl analog 47 exhibits improved antibacterial activity (MIC 80 = 0.0625 μg/mL) against S. aureus compared to platensimycin.

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Total Synthesis of Four Classes of Daphniphyllum Alkaloids

Cited by 14 publications

References 84 publications

Daphnicyclidin Alkaloids 2001–2023

Daphnicyclidin Alkaloids 2001–2023

Controllable skeletal reorganizations in natural product synthesis

Asymmetric Synthesis and Biological Evaluation of Platensilin, Platensimycin, Platencin, and Their Analogs via a Bioinspired Skeletal Reconstruction Approach

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