Total Synthesis of Bioactive Marine Meroterpenoids: The Cases of Liphagal and Frondosin B

Zong, Yan; Wang, Weijia; Xu, Tao

doi:10.3390/md16040115

Cited by 16 publications

(6 citation statements)

References 41 publications

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“… , As the inhibition of the PI3Kα-mediated biological process leads to the suppression of tumor progression, PI3Kα inhibitors are expected to serve as invaluable sources for developing anticancer agents. Because of its pronounced biological property, liphagal ( 1 ) has gained considerable attention from medicinal and synthetic chemists . In this context, successful efforts have been made independently by the groups of Andersen, , Mehta, George, Alvarez-Manzaneda, Kumar, Stoltz, Katoh, Ferreira, and Wu to chemically synthesize this natural product.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation

et al. 2020

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A synthetic route to liphagal, a natural PI3Kα inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation

et al. 2020

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“…This compound inhibited PIK-α (IC 50 = 100 nM), and was also found to be cytotoxic to several tumor cell lines with IC 50 ≈ 1 μM. It has been suggested that 106 has potential application as a new type of kinase inhibitor or even cancer drug [122]. The synthetic route of (+)-liphagal is depicted in Scheme 5, which initiates with (+)-sclareolide (commercially available) and generates the final product in ~10% yield after 13 reaction steps [122].…”

Section: Discussionmentioning

confidence: 99%

A Systematic Review of Recently Reported Marine Derived Natural Product Kinase Inhibitors

Wang

Zhang

et al. 2019

Marine Drugs

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Protein kinases are validated drug targets for a number of therapeutic areas, as kinase deregulation is known to play an essential role in many disease states. Many investigated protein kinase inhibitors are natural product small molecules or their derivatives. Many marine-derived natural products from various marine sources, such as bacteria and cyanobacteria, fungi, animals, algae, soft corals, sponges, etc. have been found to have potent kinase inhibitory activity, or desirable pharmacophores for further development. This review covers the new compounds reported from the beginning of 2014 through the middle of 2019 as having been isolated from marine organisms and having potential therapeutic applications due to kinase inhibitory and associated bioactivities. Moreover, some existing clinical drugs based on marine-derived natural product scaffolds are also discussed.

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“…94 They were isolated from marine sponges and multiple groups have contributed total synthesis studies towards these compounds. 95 The synthesis of liphagal is of particular interest, as it selectively inhibits one isoform of the phosphatidylinositide 3-kinase (PI3K) enzyme family, which is involved in cellular signaling processes. 96 The substrates 5.1.12b,c and 5.1.13c,d can be synthesized in a few steps from commercially available compounds.…”

Section: Special Topic Synthesismentioning

confidence: 99%

Recent Advances in Transition-Metal-Free (4+3)-Annulations

et al. 2021

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Abstract(4+3)-Annulations are incredibly versatile reactions which combine a 4-atom synthon and a 3-atom synthon to form both 7-membered carbocycles as well as heterocycles. We have previously reviewed transition-metal-catalyzed (4+3)-annulations. In this review, we will cover examples involving bases, NHCs, phosphines, Lewis and Brønsted acids as well as some rare examples of boronic acid catalysis and photocatalysis. In analogy to our previous review, we exclude annulations involving cyclic dienes like furan, pyrrole, cyclohexadiene or cyclopentadiene, as Chiu, Harmata, Fernándes and others have recently published reviews encompassing such substrates. We will however discuss the recent additions (2010–2020) to the literature on (4+3)-annulations involving other types of 4-atom-synthons.1 Introduction2 Bases3 Annulations Using N-Heterocyclic Carbenes3.1 N-Heterocyclic Carbenes (NHCs)3.2 N-Heterocyclic Carbenes and Base Dual-Activation4 Phosphines5 Acids5.1 Lewis Acids5.2 Brønsted Acids6 Boronic Acid Catalysis and Photocatalysis7 Conclusion

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Total Synthesis of Bioactive Marine Meroterpenoids: The Cases of Liphagal and Frondosin B

Cited by 16 publications

References 41 publications

Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation

Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation

A Systematic Review of Recently Reported Marine Derived Natural Product Kinase Inhibitors

Recent Advances in Transition-Metal-Free (4+3)-Annulations

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