Sarah Reisman

Name:

Organization: California Institute of Technology

Department: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering

Title:

TOPICS

Organic Chemistry

Asymmetric Synthesis Organic Photochemistry

Chemicals
References

Enantioselective Synthesis of (−)-Acetylapoaranotin

Co-reporter:Haoxuan Wang, Clinton J. Regan, Julian A. Codelli, Paola Romanato, Angela L. A. Puchlopek-Dermenci, and Sarah E. Reisman

Organic Letters April 7, 2017 Volume 19(Issue 7) pp:

Publication Date(Web):March 28, 2017

DOI:10.1021/acs.orglett.7b00418

The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (−)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (−)-emethallicin E and (−)-haemotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.

Chemical Synthesis of (+)-Ryanodine and (+)-20-Deoxyspiganthine

Co-reporter:Chen Xu, Arthur Han, Scott C. Virgil, and Sarah E. Reisman

ACS Central Science April 26, 2017 Volume 3(Issue 4) pp:278-278

Publication Date(Web):March 9, 2017

DOI:10.1021/acscentsci.6b00361

(+)-Ryanodine is a natural product modulator of ryanodine receptors, important intracellular calcium ion channels that play a critical role in signal transduction leading to muscle movement and synaptic transmission. Chemical derivatization of (+)-ryanodine has demonstrated that certain peripheral structural modifications can alter its pharmacology, and that the pyrrole-2-carboxylate ester is critical for high affinity binding to ryanodine receptors. However, the structural variation of available ryanodine analogues has been limited by the challenge of site-specific functionalization of semisynthetic intermediates, such as (+)-ryanodol. Here we report a synthetic strategy that provides access to (+)-ryanodine and the related natural product (+)-20-deoxyspiganthine in 18 and 19 steps, respectively. A key feature of this strategy is the reductive cyclization of an epoxide intermediate that possesses the critical pyrrole-2-carboxylate ester. This approach allows for the direct introduction of this ester in the final stage of the synthesis and provides a framework for the synthesis of previously inaccessible synthetic ryanoids.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes

Co-reporter:Kelsey E. Poremba, Nathaniel T. Kadunce, Naoyuki Suzuki, Alan H. Cherney, and Sarah E. Reisman

Journal of the American Chemical Society April 26, 2017 Volume 139(Issue 16) pp:5684-5684

Publication Date(Web):April 13, 2017

DOI:10.1021/jacs.7b01705

An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, indoles, and piperidines.

Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

Co-reporter:Naoyuki Suzuki, Julie L. Hofstra, Kelsey E. Poremba, and Sarah E. Reisman

Organic Letters April 21, 2017 Volume 19(Issue 8) pp:

Publication Date(Web):April 4, 2017

DOI:10.1021/acs.orglett.7b00793

An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.

Enantioselective Total Synthesis of (+)-Psiguadial B

Co-reporter:Lauren M. Chapman, Jordan C. Beck, Linglin Wu, and Sarah E. Reisman

Journal of the American Chemical Society 2016 Volume 138(Issue 31) pp:9803-9806

Publication Date(Web):July 24, 2016

DOI:10.1021/jacs.6b07229

The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp3)–H alkenylation reaction to strategically forge the C1–C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.

A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans

Co-reporter:Kangway V. Chuang, Madeleine E. Kieffer, and Sarah E. Reisman

Organic Letters 2016 Volume 18(Issue 18) pp:4750-4753

Publication Date(Web):September 6, 2016

DOI:10.1021/acs.orglett.6b02477

A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P(tBu)3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent total synthesis of the bisindole natural product (−)-aspergilazine A.

Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction

Co-reporter:Blake E. Daniels;Jane Ni; Sarah E. Reisman

Angewandte Chemie International Edition 2016 Volume 55( Issue 10) pp:3398-3402

Publication Date(Web):

DOI:10.1002/anie.201510972

Abstract

A conjugate addition/asymmetric protonation/aza-Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl₄ and 3,3′-dibromo-BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6-dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl₄⋅BINOL complex serves as a chiral Lewis-acid-assisted Brønsted acid.

Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction

Co-reporter:Blake E. Daniels;Jane Ni; Sarah E. Reisman

Angewandte Chemie 2016 Volume 128( Issue 10) pp:3459-3463

Publication Date(Web):

DOI:10.1002/ange.201510972

Abstract

A 15-step synthesis of (+)-ryanodol

Co-reporter:Kangway V. Chuang;Chen Xu;Sarah E. Reisman

Science 2016 Vol 353(6302) pp:912-915

Publication Date(Web):26 Aug 2016

DOI:10.1126/science.aag1028

Rapid ryanodol route

The plant-derived compound ryanodine and its hydrolyzed cousin ryanodol are biochemically interesting for their calcium-regulating capacity and chemically interesting for their dense tangle of carbon rings brimming with oxygen appendages. Chuang et al. report an efficient 15-step asymmetric synthesis of ryanodol from the structurally much simpler terpene pulegone (see the Perspective by Verdaguer). Key steps include a Pauson-Khand cyclization of a tethered alkene and alkyne with carbon monoxide to set the ring motifs, followed by an oxidation using selenium dioxide that delivers three different oxygen substituents in tandem.

Science, this issue p. 912; see also p. 866

Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds

Co-reporter:Alan H. Cherney, Nathaniel T. Kadunce, and Sarah E. Reisman

Chemical Reviews 2015 Volume 115(Issue 17) pp:9587

Publication Date(Web):August 13, 2015

DOI:10.1021/acs.chemrev.5b00162

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

Co-reporter:Nathaniel T. Kadunce;Sarah E. Reisman

Journal of the American Chemical Society 2015 Volume 137(Issue 33) pp:10480-10483

Publication Date(Web):August 9, 2015

DOI:10.1021/jacs.5b06466

A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles

Co-reporter:Alan H. Cherney ;Sarah E. Reisman

Journal of the American Chemical Society 2014 Volume 136(Issue 41) pp:14365-14368

Publication Date(Web):September 22, 2014

DOI:10.1021/ja508067c

A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.

Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents for the direct synthesis of unsymmetrical ketones

Co-reporter:Alan H. Cherney, Sarah E. Reisman

Tetrahedron 2014 70(20) pp: 3259-3265

Publication Date(Web):

DOI:10.1016/j.tet.2013.11.104

A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E

Co-reporter:John T.S. Yeoman, Jacob Y. Cha, Victor W. Mak, Sarah E. Reisman

Tetrahedron 2014 70(27–28) pp: 4070-4088

Publication Date(Web):

DOI:10.1016/j.tet.2014.03.071

Enantioselective Total Synthesis of ()-LansaiB and (+)-NocardioazinesA and B

Co-reporter:Haoxuan Wang ; Sarah E. Reisman

Angewandte Chemie International Edition 2014 Volume 53( Issue 24) pp:6206-6210

Publication Date(Web):

DOI:10.1002/anie.201402571

Abstract

The concise total syntheses of the bis(pyrroloindolines) (−)-lansai B and (+)- nocardioazines A and B are reported. The key pyrroloindoline building blocks are rapidly prepared by enantioselective formal [3+2] cycloaddition reactions. The macrocycle of (+)-nocardioazine A is constructed by an unusual intramolecular diketopiperazine formation.

Enantioselective Total Synthesis of ()-LansaiB and (+)-NocardioazinesA and B

Co-reporter:Haoxuan Wang ; Sarah E. Reisman

Angewandte Chemie 2014 Volume 126( Issue 24) pp:6320-6324

Publication Date(Web):

DOI:10.1002/ange.201402571

Abstract

A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E

Co-reporter:John T. S. Yeoman ; Victor W. Mak ;Sarah E. Reisman

Journal of the American Chemical Society 2013 Volume 135(Issue 32) pp:11764-11767

Publication Date(Web):July 25, 2013

DOI:10.1021/ja406599a

The first total syntheses of (−)-trichorabdal A and (−)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (−)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.

Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones

Co-reporter:Alan H. Cherney ; Nathaniel T. Kadunce ;Sarah E. Reisman

Journal of the American Chemical Society 2013 Volume 135(Issue 20) pp:7442-7445

Publication Date(Web):May 1, 2013

DOI:10.1021/ja402922w

The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a NiII/bis(oxazoline) catalyst in the presence of Mn0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.

α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

Co-reporter:Roger R. Nani ;Sarah E. Reisman

Journal of the American Chemical Society 2013 Volume 135(Issue 19) pp:7304-7311

Publication Date(Web):May 3, 2013

DOI:10.1021/ja401610p

An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor–acceptor-substituted diazo substrates instead produce mixtures of C–H insertion and dimerization products. α-Diazo-β-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the α-cyano-α-ketocyclopropane products are demonstrated to serve as substrates for SN2, SN2′, and aldehyde cycloaddition reactions.

Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B

Co-reporter:Madeleine E. Kieffer ; Kangway V. Chuang ;Sarah E. Reisman

Journal of the American Chemical Society 2013 Volume 135(Issue 15) pp:5557-5560

Publication Date(Web):March 29, 2013

DOI:10.1021/ja4023557

A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

Catalytic asymmetric synthesis of highly substituted pyrrolizidines

Co-reporter:Andrew D. Lim, Julian A. Codelli and Sarah E. Reisman

Chemical Science 2013 vol. 4(Issue 2) pp:650-654

Publication Date(Web):13 Nov 2012

DOI:10.1039/C2SC21617E

A catalytic asymmetric double (1,3)-dipolar cycloaddition reaction has been developed. Using a chiral silver catalyst, enantioenriched pyrrolizidines can be prepared in one flask from inexpensive, commercially available starting materials. The pyrrolizidine products contain a variety of substitution patterns and as many as six stereogenic centers.

Direct, enantioselective synthesis of pyrroloindolines and indolines from simple indole derivatives

Co-reporter:Jane Ni, Haoxuan Wang, Sarah E. Reisman

Tetrahedron 2013 69(27–28) pp: 5622-5633

Publication Date(Web):

DOI:10.1016/j.tet.2013.04.003

Recent Developments in the Catalytic, Asymmetric Construction of Pyrroloindolines Bearing All-Carbon Quaternary Stereocenters

Co-reporter:Lindsay M. Repka and Sarah E. Reisman

The Journal of Organic Chemistry 2013 Volume 78(Issue 24) pp:12314-12320

Publication Date(Web):December 2, 2013

DOI:10.1021/jo4017953

Pyrroloindoline alkaloids constitute a large family of natural products that has inspired the development of an impressive array of new reactions to prepare the key heterocyclic motif. This synopsis will address catalytic, asymmetric reactions developed to synthesize pyrroloindolines bearing C3a all-carbon quaternary stereocenters. The methods described herein include both transition-metal-catalyzed and organocatalyzed reactions that have been demonstrated to be suitable for the synthesis of the pyrroloindoline framework.

Enantioselective Synthesis of Tryptophan Derivatives by a Tandem Friedel–Crafts Conjugate Addition/Asymmetric Protonation Reaction

Co-reporter:Madeleine E. Kieffer ; Lindsay M. Repka ;Sarah E. Reisman

Journal of the American Chemical Society 2012 Volume 134(Issue 11) pp:5131-5137

Publication Date(Web):March 5, 2012

DOI:10.1021/ja209390d

The tandem Friedel–Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3′-dibromo-BINOL in the presence of stoichiometric SnCl4, and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOL·SnCl4 complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.

A copper-catalyzed arylation of tryptamines for the direct synthesis of aryl pyrroloindolines

Co-reporter:Madeleine E. Kieffer, Kangway V. Chuang and Sarah E. Reisman

Chemical Science 2012 vol. 3(Issue 11) pp:3170-3174

Publication Date(Web):17 Aug 2012

DOI:10.1039/C2SC20914D

An operationally simple, copper-catalyzed arylation of N-tosyltryptamines provides direct access to C3-aryl pyrroloindolines. A range of electron-donating and electron-withdrawing substituents is tolerated on both the indole backbone and the aryl electrophile. These reactions occur under ambient temperatures and with equimolar quantities of the coupling partners.

Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2 + 2] Cycloaddition Reaction

Co-reporter:Raul Navarro and Sarah E. Reisman

Organic Letters 2012 Volume 14(Issue 17) pp:4354-4357

Publication Date(Web):August 14, 2012

DOI:10.1021/ol3017963

Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retro-aldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating an unusual, caged, pentacyclic hemiketal product.

A Concise Total Synthesis of (−)-Maoecrystal Z

Co-reporter:Jacob Y. Cha ; John T. S. Yeoman ;Sarah E. Reisman

Journal of the American Chemical Society 2011 Volume 133(Issue 38) pp:14964-14967

Publication Date(Web):August 30, 2011

DOI:10.1021/ja2073356

The first total synthesis of (−)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective TiIII-mediated reductive epoxide coupling reaction and a diastereoselective SmII-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (−)-maoecrystal Z in only 12 steps from (−)-γ-cyclogeraniol.

Enantioselective Total Synthesis of (−)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine

Co-reporter:Julian A. Codelli ; Angela L. A. Puchlopek ;Sarah E. Reisman

Journal of the American Chemical Society 2011 Volume 134(Issue 4) pp:1930-1933

Publication Date(Web):October 24, 2011

DOI:10.1021/ja209354e

The first total synthesis of the dihydrooxepine-containing epidithiodiketopiperazine (ETP) (−)-acetylaranotin (1) is reported. The key steps of the synthesis include an enantioselective azomethine ylide (1,3)-dipolar cycloaddition reaction to set the absolute and relative stereochemistry, a rhodium-catalyzed cycloisomerization/chloride elimination sequence to generate the dihydrooxepine moiety, and a stereoretentive diketopiperazine sulfenylation to install the epidisulfide. This synthesis provides access to (−)-1 in 18 steps from inexpensive, commercially available starting materials. We anticipate that the approach described herein will serve as a general strategy for the synthesis of additional members of the dihydrooxepine ETP family.

Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone

Co-reporter:Kangway V. Chuang, Raul Navarro and Sarah E. Reisman

Chemical Science 2011 vol. 2(Issue 6) pp:1086-1089

Publication Date(Web):25 Mar 2011

DOI:10.1039/C1SC00095K

The preparation and synthetic applications of benzoquinone monoketal-derived N-tert-butanesulfinyl imines is described. These synthetically versatile intermediates undergo highly diastereoselective 1,2-addition reactions with organometallic reagents to provide 4-aminocyclohexadienones in good yields. The utility of this methodology is demonstrated in a six-step enantioselective synthesis of (–)-3-demethoxyerythratidinone.

Short, Enantioselective Total Syntheses of ()-8-Demethoxyrunanine and ()-CepharatinesA, C, and D

Co-reporter:Kangway V. Chuang;Raul Navarro ; Sarah E. Reisman

Angewandte Chemie International Edition 2011 Volume 50( Issue 40) pp:9447-9451

Publication Date(Web):

DOI:10.1002/anie.201104487

Short, Enantioselective Total Syntheses of ()-8-Demethoxyrunanine and ()-CepharatinesA, C, and D

Co-reporter:Kangway V. Chuang;Raul Navarro ; Sarah E. Reisman

Angewandte Chemie 2011 Volume 123( Issue 40) pp:9619-9623

Publication Date(Web):

DOI:10.1002/ange.201104487

Enantioselective Total Synthesis of (+)-Salvileucalin B

Co-reporter:Sergiy Levin ; Roger R. Nani ;Sarah E. Reisman

Journal of the American Chemical Society 2010 Volume 133(Issue 4) pp:774-776

Publication Date(Web):December 21, 2010

DOI:10.1021/ja110192b

An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported. Key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized norcaradiene intermediate.

Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction

Co-reporter:Lindsay M. Repka ; Jane Ni ;Sarah E. Reisman

Journal of the American Chemical Society 2010 Volume 132(Issue 41) pp:14418-14420

Publication Date(Web):September 27, 2010

DOI:10.1021/ja107328g

(R)-BINOL•SnCl4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.

Rapid Assembly of the Salvileucalin B Norcaradiene Core

Co-reporter:Sergiy Levin, Roger R. Nani and Sarah E. Reisman

Organic Letters 2010 Volume 12(Issue 4) pp:780-783

Publication Date(Web):January 20, 2010

DOI:10.1021/ol902848k

Preparation of the polycyclic core of the cytotoxic natural product salvileucalin B is described. The key feature of this synthetic strategy is a copper-catalyzed intramolecular arene cyclopropanation to provide the central norcaradiene. These studies lay the foundation for continued investigations toward an enantioselective total synthesis of 1.

Catalytic asymmetric synthesis of highly substituted pyrrolizidines

Co-reporter:Andrew D. Lim, Julian A. Codelli and Sarah E. Reisman

Chemical Science (2010-Present) 2013 - vol. 4(Issue 2) pp:NaN654-654

Publication Date(Web):2012/11/13

DOI:10.1039/C2SC21617E

Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone

Co-reporter:Kangway V. Chuang, Raul Navarro and Sarah E. Reisman

Chemical Science (2010-Present) 2011 - vol. 2(Issue 6) pp:NaN1089-1089

Publication Date(Web):2011/03/25

DOI:10.1039/C1SC00095K

A copper-catalyzed arylation of tryptamines for the direct synthesis of aryl pyrroloindolines

Co-reporter:Madeleine E. Kieffer, Kangway V. Chuang and Sarah E. Reisman