Total synthesis of racemic, natural (+) and unnatural (−) scorzocreticin

Srinivas, B.; Maadhur, Amarnath R.; Sreedhar, B.

doi:10.1016/j.tet.2014.07.107

Cited by 6 publications

(1 citation statement)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Methyl 3,5-dihydroxybenzoate was synthesized as described by Bojja 23 and colleagues. Dithiol D2 (3,5-dimercaptobenzoic acid) was synthesized by the method of Otto and Sanders, 21 beginning with the methyl 3,5-dihydroxybenzoate described above.…”

Section: Methodsmentioning

confidence: 99%

Probing the geometric constraints of RNA binding via dynamic covalent chemistry

McAnany

Reichert

Miller

2016

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

Dynamic Combinatorial Chemistry (DCC) has proven to be a reliable method for identifying hit compounds for target nucleic acid (DNA and RNA) sequences. Typically, these hit compounds are subjected to a lengthy process of optimization via traditional medicinal chemistry. Here, we examine the potential of DCC to also generate and test variations on a hit compound as a method for probing the binding site of an RNA-targeted compound. Specifically, we demonstrate that addition of linker dithiols to a disulfide library containing a known binder to the HIV-1 frameshift-stimulatory RNA (a critical regulator of the HIV life cycle) can yield a mixture of new bridged structures incorporating the dithiol, depending on dithiol structure. Equilibration of this library with the HIV FSS RNA resulted in selection of the original disulfide in preference to bridged structures, suggesting incorporation of the bridge is not compatible with this particular binding site. Application of this strategy to other RNA targets should allow for rapidly profiling the affinity of modified compounds.

show abstract

Section: Methodsmentioning

confidence: 99%

Probing the geometric constraints of RNA binding via dynamic covalent chemistry

McAnany

Reichert

Miller

2016

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Total Synthesis of Racemic, Natural (+) and Unnatural (‐) Scorzocreticin.

2015

View full text Add to dashboard Cite

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

2018

View full text Add to dashboard Cite

More than sixty years after its discovery, the Wittig reaction still is a powerful tool to create carbon–carbon double bonds. The large diversity of high‐yielding and stereoselective reactions that can be achieved, even for highly functionalized molecules, is presented, demonstrating that the Wittig reaction is an efficient and attractive strategy in synthetic organic chemistry. The principles of the reaction will be briefly presented and discussed, but the focus will be on the most recent reports using this reaction in the synthesis of heterocyclic compounds. A comprehensive discussion on its application in the total synthesis of natural products and in the synthesis of natural analogues will be presented. Emphasis will be given to important organic molecules that present interesting biological activities. The purpose of this short review is to highlight the advances in this general area by presenting such newer applications in organic synthesis and eventually guide future researchers.

show abstract

Total synthesis of racemic, natural (+) and unnatural (−) scorzocreticin

Cited by 6 publications

References 40 publications

Probing the geometric constraints of RNA binding via dynamic covalent chemistry

Probing the geometric constraints of RNA binding via dynamic covalent chemistry

ChemInform Abstract: Total Synthesis of Racemic, Natural (+) and Unnatural (‐) Scorzocreticin.

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Contact Info

Product

Resources

About