Synthesis of 2,4,6-Trisubstituted Chiral Piperidines and (−)-Dendroprimine by One-Pot Asymmetric Azaelectrocyclization Protocol

Kobayashi, Tsunetoshi; Hasegawa, Futoshi; Tanaka, Katsunori; Katsumura, Shigeo

doi:10.1021/ol0614065

Cited by 53 publications

(11 citation statements)

References 25 publications

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“…Similar strategies were applied in the stereocontrolled synthesis of (-)-dendroprimine, (+)-7-epidendroprimine, (+)-5-epidendroprimine, (+)-5,7-epidendroprimine, 65 (-)-20-epiuleinevia, 66 and (-)-dendroprimine. 67 Scheme 52…”

Section: Review Syn Thesismentioning

confidence: 99%

Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

2015

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One-pot synthesis has become an important subject of modern synthetic chemistry owing to its efficiency, versatility and expediency in constructing complicated polycyclic ring systems, especially with a sustainable and catalytic aspect. This review aims to highlight the recent advances in this area with specific emphasis on the asymmetric synthesis of natural products and related core structures as well as medicinal drugs via one-pot operation. 1 Introduction 2 Double Reactions 3 Triple Reactions 4 Quadruple Reactions 5 Pot-Economy Reactions 6 Conclusions

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Section: Review Syn Thesismentioning

confidence: 99%

Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

2015

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“…The efficiency of our rapid azaelectrocyclization protocol depends on the steric accessibility of the primary amino groups. Although reactions with internal lysines in protein tertiary structures and N-terminal amines (secondary amine) are very slow (>5 h at 24 C) [79], lysines at the protein's surface react rapidly (10-30 min at 24 C) and, therefore, labeling occurs preferentially at surface positions. Moreover, dihydropyridines as the electrocyclization products, which retain cationic charges as those of the inherent lysines, should contribute to the retention of the protein activity.…”

Section: Azaelectrocyclization-based Labeling Of Lysines; New Microgrmentioning

confidence: 99%

Chemical Approach to a Whole Body Imaging of Sialo-N-Linked Glycans

Tanaka

Fukase

2014

Topics in Current Chemistry

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PET and noninvasive fluorescence imaging of the sialo-N-linked glycan derivatives are described. To establish the efficient labeling protocol for N-glycans and/or glycoconjugates, new labeling probes of fluorescence and ⁶⁸Ga-DOTA, as the positron emission nucleus for PET, through rapid 6π-azaelectrocyclization were designed and synthesized, (E)-ester aldehydes. The high reactivity of these probes enabled the labeling of lysine residues in peptides, proteins, and even amino groups on the cell surfaces at very low concentrations of the target molecules (~10⁻⁸ M) within a short reaction time (~5 min) to result in "selective" and "non-destructive" labeling of the more accessible amines. The first MicroPET of glycoproteins, ⁶⁸Ga-DOTA-orosomucoid and asialoorosomucoid, successfully visualized the differences in the circulatory residence of glycoproteins, in the presence or absence of sialic acids. In vivo dynamics of the new N-glycoclusters, prepared by the "self-activating" Huisgen cycloaddition reaction, could also be affected significantly by their partial structures at the non-reducing end, i.e., the presence or absence of sialic acids, and/or sialoside linkages to galactose. Azaelectrocyclization chemistry is also applicable to the engineering of the proteins and/or the cell surfaces by the oligosaccharides; lymphocytes chemically engineered by sialo-N-glycan successfully target the tumor implanted in BALB/C nude mice, detected by noninvasive fluorescence imaging.

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“…This powerful methodology was applied to the total synthesis of three natural indole alkaloids, such as (-)-dendroprimine, 211 (-)-corynantheidine, 212 and (-)-20-epiuleine, 213 Diastereoselective nickel-catalysed asymmetric four-component domino Reformatsky reactions have been developed by Dondoni et al with the aim of achieving chiral C-glycosyl b-amino esters. 138 As shown in Scheme 1.125, an in situ initial coupling of chiral C-glycosyl aldehydes with p-methoxybenzylamine gave the corresponding imines.…”

Section: Multicomponent Reactions Based On the Petasis Reactionmentioning

confidence: 99%

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

2013

Asymmetric Domino Reactions

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This chapter updates the recent developments in asymmetric one-, two-, and multicomponent domino reactions which involve chiral substrates. It is divided into two sections, dealing successively with one- and two-component domino reactions, and with multicomponent domino reactions. The first section is subdivided into eight sections, describing domino reactions with an anionic primary step, domino reactions based on cationic sequences, domino reactions initiated by a pericyclic primary step, domino reactions based on carbene sequences, palladium-catalysed domino reactions, ruthenium-catalysed domino reactions, gold-catalysed domino reactions, and finally miscellaneous domino reactions. The second section of the chapter is subdivided into 10 sections, dealing with multicomponent reactions initiated by the Michael addition, multicomponent reactions based on the Hantzsch reaction, multicomponent reactions based on the Ugi reaction, multicomponent reactions based on the Strecker reaction, multicomponent reactions based on the Mannich reaction, multicomponent reactions initiated by an allylation reaction, multicomponent reactions based on the Passerini reaction, multicomponent reactions based on the Biginelli reaction, multicomponent reactions based on the Petasis reaction, and finally miscellaneous multicomponent reactions. The power and utility of these reactions are well illustrated by their application in the synthesis of a wide range of structurally diverse and complex chiral molecules.

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Synthesis of 2,4,6-Trisubstituted Chiral Piperidines and (−)-Dendroprimine by One-Pot Asymmetric Azaelectrocyclization Protocol

Cited by 53 publications

References 25 publications

Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

Chemical Approach to a Whole Body Imaging of Sialo-N-Linked Glycans

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

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