Steven M. Weinreb

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Total Syntheses of the Monoterpenoid Indole Alkaloids (±)‐Alstoscholarisine B and C

Jeremy D. Mason, Steven M. Weinreb

Angewandte Chemie International Edition > 56 > 52 > 16674 - 16676

Total syntheses of the monoterpenoid indole alkaloids (±)‐alstoscholarisine B and C were accomplished starting from a readily available indole‐2‐acetic ester and an α,β‐unsaturated N‐sulfonyllactam.

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Total Syntheses of the Monoterpenoid Indole Alkaloids (±)‐Alstoscholarisine B and C

Jeremy D. Mason, Steven M. Weinreb

Angewandte Chemie > 129 > 52 > 16901 - 16903

Total syntheses of the monoterpenoid indole alkaloids (±)‐alstoscholarisine B and C were accomplished starting from a readily available indole‐2‐acetic ester and an α,β‐unsaturated N‐sulfonyllactam.

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N-sulfonyl imines — Useful synthons in stereoselective organic synthesis

Steven M. Weinreb

Topics in Current Chemistry > Stereoselective Heterocyclic Synthesis II > 131-184

Until recently, N-sulfonyl imines had found only limited and sporadic use in organic synthesis. During the past decade, however, it has become increasingly clear that these species are valuable synthons and are capable of undergoing many unique transformations. A comprehensive review of the chemistry of these compounds is presented here with particular emphasis on their applications in stereoselective...

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Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)‐Myrioneurinol

Anthony J. Nocket, Steven M. Weinreb

Angewandte Chemie > 126 > 51 > 14386 - 14389

The first total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid (±)‐myrioneurinol has been accomplished using three highly diastereoselective reactions as pivotal steps: 1) an intramolecular Michael addition of a benzyloxycarbonyl‐protected lactam titanium enolate to an α,β‐unsaturated ester for construction of the spirocyclic C5 quaternary center and the a/d rings, 2) a malonate anion...

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Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)‐Myrioneurinol

Anthony J. Nocket, Steven M. Weinreb

Angewandte Chemie International Edition > 53 > 51 > 14162 - 14165

The first total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid (±)‐myrioneurinol has been accomplished using three highly diastereoselective reactions as pivotal steps: 1) an intramolecular Michael addition of a benzyloxycarbonyl‐protected lactam titanium enolate to an α,β‐unsaturated ester for construction of the spirocyclic C5 quaternary center and the a/d rings, 2) a malonate anion...

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Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)‐Alstilobanine A

Yiqing Feng, Max M. Majireck, Steven M. Weinreb

Angewandte Chemie > 124 > 51 > 13018 - 13021

Das tetracyclische Monoterpen‐Alkaloid Alstilobanin A wurde in racemischer Form erhalten. Wichtige Stufen seiner Totalsynthese sind eine neuartige konjugierte Addition eines Esterenolats an ein Nitrosoalken sowie eine intramolekulare formale [2+2]‐Cycloaddition zur Bildung eines β‐Lactons für die cis‐verknüpfte 2‐Azadecalin‐Einheit des Alkaloids. TMSE=Trimethylsilylethoxy, Ts=4‐Toluolsulfonyl.

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Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)‐Alstilobanine A

Yiqing Feng, Max M. Majireck, Steven M. Weinreb

Angewandte Chemie International Edition > 51 > 51 > 12846 - 12849

Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β‐lactone to generate the requisite cis‐fused 2‐azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4‐toluenesulfonyl.

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Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Joshua R. Sacher, Steven M. Weinreb

Tetrahedron > 2011 > 67 > 52 > 10203- 10207

A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective Diels–Alder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at...

article

Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes

Ritobroto Sengupta, Jason A. Witek, Steven M. Weinreb

Tetrahedron > 2011 > 67 > 43 > 8229-8234

Intermolecular Michael-type conjugate additions of some in situ-generated ring-substituted nitrosocyclohexenes with both carbon- and heteronucleophiles have been found to be highly stereoselective, leading predominantly (or exclusively) to products resulting from axial attack on a half-chair conformation of the nitrosoalkene substrate.

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Further Studies of Intramolecular Michael Reactions of Nitrosoalkenes for Construction of Functionalized Bridged Ring Systems

Praveen Kumar, Puhui Li, Ilia Korboukh, Tony L. Wang, more

The Journal of Organic Chemistry > 2011 > 76 > 7 > 2094 - 2101

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Investigation of the Stereochemistry of Intermolecular Conjugate Additions of Nucleophiles to Acyclic Nitrosoalkenes

Jason A. Witek, Steven M. Weinreb

Organic Letters > 2011 > 13 > 5 > 1258 - 1260

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An expedient reductive method for conversion of ketoximes to the corresponding carbonyl compounds

Max M. Majireck, Jason A. Witek, Steven M. Weinreb

Tetrahedron Letters > 2010 > 51 > 27 > 3555-3557

A wide array of readily prepared pivalates of ketoximes can be converted to the corresponding ketones in good yields by treatment with iron powder in THF containing catalytic amounts of both trimethylsilyl chloride and glacial acetic acid at room temperature for 30min, followed by a brief aqueous workup.

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Evolution of a Strategy for Total Synthesis of the Marine Fungal Alkaloid (±)-Communesin F

Jae Hong Seo, Peng Liu, Steven M. Weinreb

The Journal of Organic Chemistry > 2010 > 75 > 8 > 2667 - 2680

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Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles

Puhui Li, Max M. Majireck, Jason A. Witek, Steven M. Weinreb

Tetrahedron Letters > 2010 > 51 > 15 > 2032-2035

A diverse array of nitrosoalkenes derived from both acyclic and cyclic ketones, as well as aldehydes, via the Denmark protocol using α-chloro-O-TBS-oximes can be trapped efficiently in situ by a wide variety of potassium ester enolates to afford conjugate addition products in good yields.

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Total Synthesis of the Polycyclic Fungal Metabolite (±)‐Communesin F

Peng Liu, Jae Hong Seo, Steven M. Weinreb

Angewandte Chemie > 122 > 11 > 2044 - 2047

Eine Rarität: Das heptacyclische Pilzalkaloid Communesin F war das Ziel einer Totalsynthese, die eine ungewöhnliche intramolekulare Heck‐Cyclisierung eines tetrasubstituierten Alkens, eine reduktive Cyclisierung eines N‐Boc‐Anilins, eine stereoselektive C‐Allylierung eines Lactams sowie eine Folge aus Azidreduktion und N‐Boc‐δ‐lactam‐Ringöffnung umfasst (siehe Schema, BOM=Benzyloxymethyl).

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Total Synthesis of the Polycyclic Fungal Metabolite (±)‐Communesin F

Peng Liu, Jae Hong Seo, Steven M. Weinreb

Angewandte Chemie International Edition > 49 > 11 > 2000 - 2003

What the Heck: The heptacyclic fungal alkaloid communesin F was the target of a total synthesis featuring a rare example of an intramolecular Heck cyclization of a tetrasubstituted alkene, a reductive cyclization of an N‐Boc aniline, a stereoselective C allylation of a lactam, and an azide reduction/N‐Boc‐δ‐lactam ring opening sequence (see scheme, BOM=benzyloxymethyl).

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Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

Michael A. Evans, Joshua R. Sacher, Steven M. Weinreb

Tetrahedron > 2009 > 65 > 33 > 6712-6719

A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produce the C-4/20 vicinal quaternary centers having the requisite relative configuration of the metabolite.

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Total Synthesis of the Securinega Alkaloid (−)-Secu’amamine A

Peng Liu, Sungwoo Hong, Steven M. Weinreb

Journal of the American Chemical Society > 2008 > 130 > 24 > 7562 - 7563

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A mild, efficient method for the oxidation of α-diazo-β-hydroxyesters to α-diazo-β-ketoesters

Puhui Li, Max M. Majireck, Ilia Korboukh, Steven M. Weinreb

Tetrahedron Letters > 2008 > 49 > 19 > 3162-3164

A wide variety of α-diazo-β-ketoesters can be prepared in good overall yields via a two-step sequence involving addition of ethyl lithiodiazoacetate to aliphatic, aromatic, and conjugated aldehydes followed by mild oxidation with the Dess–Martin periodinane.

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A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization

Matthew L. Meketa, Steven M. Weinreb

Tetrahedron > 2007 > 63 > 37 > 9112-9119

A second generation total synthesis of the marine sponge metabolite ageladine A utilizing a biogenetically inspired 6π-2-azaelectrocyclization of triene 34 as the key step is performed to construct the imidazopyridine core of the metabolite.

INFONA - science communication portal

Search results for: Steven M. Weinreb

Total Syntheses of the Monoterpenoid Indole Alkaloids (±)‐Alstoscholarisine B and C

Total Syntheses of the Monoterpenoid Indole Alkaloids (±)‐Alstoscholarisine B and C

N-sulfonyl imines — Useful synthons in stereoselective organic synthesis

Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)‐Myrioneurinol

Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)‐Myrioneurinol

Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)‐Alstilobanine A

Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)‐Alstilobanine A

Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes

Further Studies of Intramolecular Michael Reactions of Nitrosoalkenes for Construction of Functionalized Bridged Ring Systems

Investigation of the Stereochemistry of Intermolecular Conjugate Additions of Nucleophiles to Acyclic Nitrosoalkenes

An expedient reductive method for conversion of ketoximes to the corresponding carbonyl compounds

Evolution of a Strategy for Total Synthesis of the Marine Fungal Alkaloid (±)-Communesin F

Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles

Total Synthesis of the Polycyclic Fungal Metabolite (±)‐Communesin F

Total Synthesis of the Polycyclic Fungal Metabolite (±)‐Communesin F

Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine

Total Synthesis of the Securinega Alkaloid (−)-Secu’amamine A

A mild, efficient method for the oxidation of α-diazo-β-hydroxyesters to α-diazo-β-ketoesters

A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization

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