Total and formal syntheses of fostriecin

Gao, Dong; Li, Bohui; O’Doherty, George A.

doi:10.1039/d0qo01121e

Cited by 3 publications

(2 citation statements)

References 70 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There have been various reports on the total synthesis of fostriecin since its discovery. In order to contribute to the facile synthesis of this naturally occurring polyketide, Dong et al [ 70 ] in 2020 reported a facile synthetic route for its total synthesis. In their methodology, trienyne 104 was converted to compound 105 via several steps.…”

Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

View full text Add to dashboard Cite

Sharpless asymmetric dihydroxylation is an important reaction in the enantioselective synthesis of chiral vicinal diols that involves the treatment of alkene with osmium tetroxide along with optically active quinine ligand. Sharpless introduced this methodology after considering the importance of enantioselectivity in the total synthesis of medicinally important compounds. Vicinal diols, produced as a result of this reaction, act as intermediates in the synthesis of different naturally occurring compounds. Hence, Sharpless asymmetric dihydroxylation plays an important role in synthetic organic chemistry due to its undeniable contribution to the synthesis of biologically active organic compounds. This review emphasizes the significance of Sharpless asymmetric dihydroxylation in the total synthesis of various natural products, published since 2020.

show abstract

Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Unfortunately, this study was terminated before reaching the MTD due to instability in storage and unpredictable purity . Nowadays, although the synthesis problem of fostriecin has been solved, the storage stability of fostriecin is still a problem that urgently needs to be addressed. − When combined with carboplatin in ovarian cancer therapy, fostriecin can increase chemosensitivity, DNA damage, and micronuclei formation . The underlying antitumor mechanism includes the regulation of the DDR pathway mediated by PP4 .…”

Section: Small-molecule Modulators Of Pppasesmentioning

confidence: 99%

Strategies for Targeting Serine/Threonine Protein Phosphatases with Small Molecules in Cancer

et al. 2021

View full text Add to dashboard Cite

Among numerous posttranslational regulation patterns, phosphorylation is reversibly controlled by the balance of kinases and phosphatases. The major form of cellular signaling involves the reversible phosphorylation of proteins on tyrosine, serine, or threonine residues. However, altered phosphorylation levels are found in diverse diseases, including cancer, making kinases and phosphatases ideal drug targets. In contrast to the success of prosperous kinase inhibitors, design of small molecules targeting phosphatase is struggling due to past bias and difficulty. This is especially true for serine/threonine phosphatases, one of the largest phosphatase families. From this perspective, we aim to provide insights into serine/threonine phosphatases and the small molecules targeting these proteins for drug development, especially in cancer. Through highlighting the modulation strategies, we aim to provide basic principles for the design of small molecules and future perspectives for the application of drugs targeting serine/threonine phosphatases.

show abstract

Cobalt catalyzed practical hydroboration of terminal alkynes with time-dependent stereoselectivity

Wen,

Huang,

Zhang

et al. 2024

Nat Commun

View full text Add to dashboard Cite

Stereodefined vinylboron compounds are important organic synthons. The synthesis of E−1-vinylboron compounds typically involves the addition of a B-H bond to terminal alkynes. The selective generation of the thermodynamically unfavorable Z-isomers remains challenging, necessitating improved methods. Here, such a proficient and cost-effective catalytic system is introduced, comprising a cobalt salt and a readily accessible air-stable CNC pincer ligand. This system enables the transformation of terminal alkynes, even in the presence of bulky substituents, with excellent Z-selectivity. High turnover numbers (>1,600) and turnover frequencies (>132,000 h−1) are achieved at room temperature, and the reaction can be scaled up to 30 mmol smoothly. Kinetic studies reveal a formal second-order dependence on cobalt concentration. Mechanistic investigations indicate that the alkynes exhibit a higher affinity for the catalyst than the alkene products, resulting in exceptional Z-selective performance. Furthermore, a rare time-dependent stereoselectivity is observed, allowing for quantitative conversion of Z-vinylboronate esters to the E-isomers.

show abstract

Total and formal syntheses of fostriecin

Abstract: Two formal syntheses and one total synthesis of fostriecin (1) have been achieved, as well as, the synthesis of its related congener dihydro-dephospho-fostriecin. All the routes use the Sharpless dihydroxylation...

Cited by 3 publications

References 70 publications

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Strategies for Targeting Serine/Threonine Protein Phosphatases with Small Molecules in Cancer

Cobalt catalyzed practical hydroboration of terminal alkynes with time-dependent stereoselectivity

Contact Info

Product

Resources

About