Latest Articles of Synlett


Formation of a Novel C11-Acetone Adduct of a Pyrrolobenzodiazepine (PBD) with Loss of Cytotoxicity 10.1055/s-0036-1591552 2018-04-10 The pyrrolidine-catalysed formation of novel diastereomeric C11-acetone adducts was observed during the chromatographic purification of pyrrolobenzodiazepine (PBD) compounds in the presence of acetone. The mechanism of this reaction was explored and the adduc...
Convergent Synthesis of Novel Mono- and Di-substituted 1,2-Isopropylideneglucofuranose Appended Dendrimers with a Ferrocene Core and their Electrochemical Studies 10.1055/s-0037-1609490 2018-04-10 Ferrocene-cored dendrimers incorporating 1,2-isopropylidenefuranose capped furanoside branches were synthesized and their electrochemical properties were studied. It was observed that the dendritic environment in the ferrocene dendrimers increased the E 1/2 v...
Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions 10.1055/s-0036-1591982 2018-04-09 Lewis bases were evaluated as catalysts for halocarbocyclization reactions of alkynylstyrenes and a cinnamylaniline derivative. Phosphines and phosphorus chalcogenides exhibited high activity for the conversion of alkynylstyrenes in the presence of N-halosucc...
Controlled Aerobic Oxidation of Primary Benzylic Alcohols to Aldehydes Catalyzed by Polymer-Supported Triazine-Based Dendrimer–Copper Composites 10.1055/s-0036-1591981 2018-04-09 A controlled aerobic oxidation of primary benzylic alcohols to the corresponding benzaldehydes by using polystyrene–poly(ethylene glycol) (PS–PEG) resin-supported triazine-based polyethyleneamine dendrimer–copper complexes [PS–PEG-TD2–Cu(II)] was developed. ...
Skeletal Rearrangements as Strategies for the Total Syntheses of Indole Alkaloids 10.1055/s-0036-1591560 2018-04-04 In this account, we summarize our recent efforts in the total syntheses of several indole alkaloids, including minfiensine, calophyline A, deformylcorymine, strictamine, and goniomitine. Our central theme is to utilize skeletal rearrangements as key strategie...
Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1,n-Diamines 10.1055/s-0036-1591550 2018-04-04 A two-step sequence was developed for the synthesis of chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazine-13-carboxylates and -diazepine-14-carboxylates by the reaction of substituted dimethyl 2-(3-acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1,n-diamines at room temper...
PPh3-Mediated [3+2] Cycloaddition Reaction between Bis-Substituted Allenoate and N-Tosylaldimines to Construct 2-Pyrrolines 10.1055/s-0037-1609489 2018-03-28 A triphenylphosphine-promoted [3+2] cycloaddition of α,γ-bis-substituted allenoates and N-tosylaldimines followed by alkene isomerization was disclosed, affording a series of functionalized 2-pyrroline derivatives in moderate chemical yields with random diast...
Synthesis of Nepetoidin B 10.1055/s-0036-1591556 2018-03-28 The first synthesis of nepetoidin B in an overall yield of 17% was achieved in two steps through Baeyer–Villiger oxidation of commercially available 1,5-bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one with oxone to produce the tetramethylated nepetoidin B, follo...
Synthetic Transformations of Alkenyl MIDA Boronates toward the Efficient Construction of Organoborons 10.1055/s-0036-1591958 2018-03-28 The attachment of N-methyliminodiacetyl boron (MIDA boron) to alkenes leads to a new type of activated alkenes. Synthetic manipulation of the alkene double bond while retaining the boron moiety offers an unprecedented opportunity for the construction of organ...
Facile Access to 1,5-Benzodiazepines via Amine-Promoted (4+3) Annulations of δ-Acetoxy Allenoates with o-Diaminobenzenes under Mild Conditions 10.1055/s-0037-1609347 2018-03-23 An amine-promoted (4+3) annulation of δ-acetoxy allenoate with o-diaminobenzene is reported, providing a facile access to 1,5-benzodiazepine. This method features wide reaction scope, mild conditions, and readily available starting materials. The cascade reac...

Formation of a Novel C11-Acetone Adduct of a Pyrrolobenzodiazepine (PBD) with Loss of Cytotoxicity

10.1055/s-0036-1591552

2018-04-10

The pyrrolidine-catalysed formation of novel diastereomeric C11-acetone adducts was observed during the chromatographic purification of pyrrolobenzodiazepine (PBD) compounds in the presence of acetone. The mechanism of this reaction was explored and the adduc...

Convergent Synthesis of Novel Mono- and Di-substituted 1,2-Isopropylideneglucofuranose Appended Dendrimers with a Ferrocene Core and their Electrochemical Studies

10.1055/s-0037-1609490

2018-04-10

Ferrocene-cored dendrimers incorporating 1,2-isopropylidenefuranose capped furanoside branches were synthesized and their electrochemical properties were studied. It was observed that the dendritic environment in the ferrocene dendrimers increased the E 1/2 v...

Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions

10.1055/s-0036-1591982

2018-04-09

Lewis bases were evaluated as catalysts for halocarbocyclization reactions of alkynylstyrenes and a cinnamylaniline derivative. Phosphines and phosphorus chalcogenides exhibited high activity for the conversion of alkynylstyrenes in the presence of N-halosucc...

Controlled Aerobic Oxidation of Primary Benzylic Alcohols to Aldehydes Catalyzed by Polymer-Supported Triazine-Based Dendrimer–Copper Composites

10.1055/s-0036-1591981

2018-04-09

A controlled aerobic oxidation of primary benzylic alcohols to the corresponding benzaldehydes by using polystyrene–poly(ethylene glycol) (PS–PEG) resin-supported triazine-based polyethyleneamine dendrimer–copper complexes [PS–PEG-TD2–Cu(II)] was developed. ...

Skeletal Rearrangements as Strategies for the Total Syntheses of Indole Alkaloids

10.1055/s-0036-1591560

2018-04-04

In this account, we summarize our recent efforts in the total syntheses of several indole alkaloids, including minfiensine, calophyline A, deformylcorymine, strictamine, and goniomitine. Our central theme is to utilize skeletal rearrangements as key strategie...

Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1,n-Diamines

10.1055/s-0036-1591550

2018-04-04

A two-step sequence was developed for the synthesis of chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazine-13-carboxylates and -diazepine-14-carboxylates by the reaction of substituted dimethyl 2-(3-acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1,n-diamines at room temper...

PPh3-Mediated [3+2] Cycloaddition Reaction between Bis-Substituted Allenoate and N-Tosylaldimines to Construct 2-Pyrrolines

10.1055/s-0037-1609489

2018-03-28

A triphenylphosphine-promoted [3+2] cycloaddition of α,γ-bis-substituted allenoates and N-tosylaldimines followed by alkene isomerization was disclosed, affording a series of functionalized 2-pyrroline derivatives in moderate chemical yields with random diast...

Synthesis of Nepetoidin B

10.1055/s-0036-1591556

2018-03-28

The first synthesis of nepetoidin B in an overall yield of 17% was achieved in two steps through Baeyer–Villiger oxidation of commercially available 1,5-bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one with oxone to produce the tetramethylated nepetoidin B, follo...

Synthetic Transformations of Alkenyl MIDA Boronates toward the Efficient Construction of Organoborons

10.1055/s-0036-1591958

2018-03-28

The attachment of N-methyliminodiacetyl boron (MIDA boron) to alkenes leads to a new type of activated alkenes. Synthetic manipulation of the alkene double bond while retaining the boron moiety offers an unprecedented opportunity for the construction of organ...

Facile Access to 1,5-Benzodiazepines via Amine-Promoted (4+3) Annulations of δ-Acetoxy Allenoates with o-Diaminobenzenes under Mild Conditions

10.1055/s-0037-1609347

2018-03-23

An amine-promoted (4+3) annulation of δ-acetoxy allenoate with o-diaminobenzene is reported, providing a facile access to 1,5-benzodiazepine. This method features wide reaction scope, mild conditions, and readily available starting materials. The cascade reac...