Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Hatakeyama, Susumi

doi:10.1248/cpb.c14-00474

Cited by 7 publications

References 119 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Synthesis of Pyrrolidones and Caprolactams by Intramolecular Cyclization of Linear Precursors

Arthur

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

View full text Add to dashboard Cite

Pyrrolidones and caprolactams are important molecules, serving functions ranging from their use as solvents and surfactants to their occurrence in natural products and drugs. This chapter is devoted to the synthesis of pyrrolidones and caprolactams by intramolecular ring‐forming reactions. Perhaps the simplest heterolytic cyclization to envision is the attack of an amine group onto a carboxylic acid derivative, forming the amide C–N linkage. Pyrrolidones can be created by carboxamide radical cyclization onto an alkene. Amidyl radicals can activate remote C–H bonds to cyclization. The chapter presents the synthesis of pyrrolidones and caprolactams by homolytic (radical), carbene insertion and metathetic cyclization reactions. Carbenoid attack on an electron‐rich aromatic ring competes favorably with insertion into alkane C–H. Olefin metathesis is a metal‐catalyzed reaction that entails the redistribution of alkene carbons by the scission and regeneration of carbon–carbon double bonds.

show abstract

Synthesis of Pyrrolidones and Caprolactams by Intramolecular Cyclization of Linear Precursors

Arthur

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

View full text Add to dashboard Cite

show abstract

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Biesen,

Müller

2023

Chemistry A European J

View full text Add to dashboard Cite

Aroyl‐S,N‐ketene acetals represent a peculiar class of heterocyclic merocyanines, compounds bearing pronounced and rather short dipoles with great push‐pull characteristics that define their rich properties. They are accessible via a wide array of synthetic concepts and procedures, ranging from addition‐elimination and condensation procedures up to rearrangement and metal‐mediated reactions. With our work from 2020, aroyl‐S,N‐ketene acetals have been identified as powerful and promising dyes with pronounced and vastly tunable solid‐state emission and aggregation‐induced emission properties. One characteristic trademark of this class of dye molecules is the level of control that could be exerted, and which was thoroughly explored. Based on these results, the field was opened to extend the system to bi‐ and multichromophoric systems by the full toolkit of synthetic organic chemistry thus giving access to even more exciting properties and manifolded substance libraries capitalizing on the AIE properties. This review aims at outlining the reaction‐based principles that allow for a swift and facile access to aroyl‐S,N‐ketene acetals, their methodical and structural evolution and the plethora of fluorescence and aggregation properties.

show abstract

ChemInform Abstract: Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Hatakeyama

2015

ChemInform

View full text Add to dashboard Cite

show abstract

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Cited by 7 publications

References 119 publications

Synthesis of Pyrrolidones and Caprolactams by Intramolecular Cyclization of Linear Precursors

Synthesis of Pyrrolidones and Caprolactams by Intramolecular Cyclization of Linear Precursors

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

ChemInform Abstract: Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Contact Info

Product

Resources

About