Synthetic approaches towards alkaloids bearing α-tertiary amines

Enantioselective total synthesis of (+)-methoxystemofoline and (+)-isomethoxystemofoline

(2015) Pei-Qiang Huang et al.   CHEMICAL COMMUNICATIONS

Late Transition Metal-Catalyzed Hydroamination and Hydroamidation

(2015) Liangbin Huang et al.   CHEMICAL REVIEWS

Aza-Quaternary Scaffolds from Selective Bond Cleavage of Bridgehead-Substituted 7-Azabicyclo[2.2.1]heptane: Total Synthesis of (+)-Cylindricines C-E and (−)-Lepadiformine A

(2015) Ganesh Pandey et al.   CHEMISTRY-A EUROPEAN JOURNAL

Metal-catalysed azidation of tertiary C–H bonds suitable for late-stage functionalization

(2015) Ankit Sharma et al.   NATURE

Total Synthesis of (+)-3-Demethoxyerythratidinone and (+)-Erysotramidine via the Oxidative Amidation of a Phenol

(2015) Marco Paladino et al.   ORGANIC LETTERS

Total Synthesis of (−)-N-Methylwelwitindolinone C Isothiocyanate Based on a Pd-Catalyzed Tandem Enolate Coupling Strategy

(2015) Keita Komine et al.   ORGANIC LETTERS

A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

(2015) Hieu-Trinh Luu et al.   ORGANIC LETTERS

Unified approach to prenylated indole alkaloids: total syntheses of (−)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I

(2015) Eduardo V. Mercado-Marin et al.   Chemical Science

Total Synthesis of (−)-Lundurine A and Determination of its Absolute Configuration

(2014) Shuaijiang Jin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Corrigendum: A Concise and Versatile Synthesis of Alkaloids fromKopsia tenuis: Total Synthesis of (±)-Lundurine A and B

(2014) Shigeru Arai et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Decarbonylative Radical Coupling of α-Aminoacyl Tellurides: Single-Step Preparation of γ-Amino and α,β-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

(2014) Masanori Nagatomo et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

A Concise and Versatile Synthesis of Alkaloids fromKopsia tenuis: Total Synthesis of (±)-Lundurine A and B

(2014) Shigeru Arai et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Synthesis of Gracilamine

(2014) Yingbo Shi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Biogenetically Inspired Total Syntheses of Lycopodium Alkaloids, (+)-Flabellidine and (−)-Lycodine

(2014) Masayuki Azuma et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (−)-N-Methylwelwitindolinone B Isothiocyanate via a Chlorinative Oxabicycle Ring-Opening Strategy

(2014) Nicholas A. Weires et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Unified Strategy for the Synthesis of 7-Membered-Ring-Containing Lycopodium Alkaloids

(2014) Amy S. Lee et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total synthesis and isolation of citrinalin and cyclopiamine congeners

(2014) Eduardo V. Mercado-Marin et al.   NATURE

Application of Two Direct C(sp3)–H Functionalizations for Total Synthesis of (+)-Lactacystin

(2014) Shun Yoshioka et al.   ORGANIC LETTERS

Correction to Total Synthesis of (−)-Histrionicotoxin

(2014) Yohei Adachi et al.   ORGANIC LETTERS

Total Synthesis of (±)-Lundurine B

(2014) Masaki Hoshi et al.   ORGANIC LETTERS

Enantiospecific Total Synthesis ofN-Methylwelwitindolinone D Isonitrile

(2013) Evan D. Styduhar et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Divergent and Efficient Syntheses of theLycopodiumAlkaloids (−)-Lycojaponicumin C, (−)-8-Deoxyserratinine, (+)-Fawcettimine, and (+)-Fawcettidine

(2013) Si-Hua Hou et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Protic-Solvent-Mediated Cycloisomerization of Quinoline and Isoquinoline Propargylic Alcohols: Syntheses of (±)-3-Demethoxyerythratidinone and (±)-Cocculidine

(2013) Stephen T. Heller et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Syntheses of (−)-Acutumine and (−)-Dechloroacutumine

(2013) Sandra M. King et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Development of Enantioselective Synthetic Routes to the Hasubanan and Acutumine Alkaloids

(2013) Nicholas A. Calandra et al.   JOURNAL OF ORGANIC CHEMISTRY

Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions

(2013) Changxia Yuan et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective Total Synthesis of (−)-Citrinadin A and Revision of Its Stereochemical Structure

(2013) Zhiguo Bian et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

An Enantioselective Total Synthesis and Stereochemical Revision of (+)-Citrinadin B

(2013) Ke Kong et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (±)-Gelsemoxonine

(2013) Stefan Diethelm et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rapid Access to Spirocyclic Oxindole Alkaloids: Application of the Asymmetric Palladium-Catalyzed [3 + 2] Trimethylenemethane Cycloaddition

(2013) Barry M. Trost et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthesis of (±)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement

(2013) Arash Soheili et al.   ORGANIC LETTERS

Asymmetric Intermolecular Conjugate Addition of Amino Acid Derivatives via Memory of Chirality: Total Synthesis of Manzacidin A

(2013) Tomoyuki Yoshimura et al.   ORGANIC LETTERS

A Novel Synthesis of (−)-Huperzine A via Tandem Intramolecular Aza-Prins Cyclization–Cyclobutane Fragmentation

(2013) James D. White et al.   ORGANIC LETTERS

Total Synthesis of Kopsinine

(2013) Jian Xie et al.   ORGANIC LETTERS

Potentially Biomimetic Total Synthesis and Relative Stereochemical Assignment of (±)-Gracilamine

(2012) Songchuan Tian et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Syntheses of All the Amathaspiramides

(2012) Koji Chiyoda et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective Formal Total Syntheses of Didehydrostemofoline and Isodidehydrostemofoline through a Catalytic Dipolar Cycloaddition Cascade

(2012) Chao Fang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Biomimetic Total Synthesis of (+)-Gelsemine

(2012) Xuan Zhou et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

(2012) Hao-Hua Huo et al.   JOURNAL OF ORGANIC CHEMISTRY

Progress toward the Syntheses of (+)-GB 13, (+)-Himgaline, and Himandridine. New Insights into Intramolecular Imine/Enamine Aldol Cyclizations

(2012) David A. Evans et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects

(2012) Hajer Abdelkafi et al.   NATURAL PRODUCT REPORTS

Welwitindolinone is well worth it

(2012) John L. Wood   Nature Chemistry

Formal Syntheses of Naturally Occurring Welwitindolinones

(2012) Tsung-hao Fu et al.   ORGANIC LETTERS

Total Synthesis of (−)-FR901483

(2012) Ai-Jun Ma et al.   ORGANIC LETTERS

Practical Syntheses of Proposed and Revised Manzacidin B and Their Congeners

(2012) Kuppusamy Sankar et al.   ORGANIC LETTERS

An Efficient Total Synthesis of (−)-Huperzine A

(2012) Rui Ding et al.   ORGANIC LETTERS

A Formal Enantioselective Total Synthesis of FR901483

(2012) Hao-Hua Huo et al.   ORGANIC LETTERS

Development of a Large-Scale Synthetic Route to Manufacture (−)-Huperzine A

(2012) Stephen R. Tudhope et al.   ORGANIC PROCESS RESEARCH & DEVELOPMENT

Total Synthesis Guided Structure Elucidation of (+)-Psychotetramine

(2011) Klement Foo et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Efficient Entry to the Hasubanan Alkaloids: First Enantioselective Total Syntheses of (−)-Hasubanonine, (−)-Runanine, (−)-Delavayine, and (+)-Periglaucine B

(2011) Seth B. Herzon et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Syntheses of Lycopodium Alkaloids (+)-Fawcettimine, (+)-Fawcettidine, and (−)-8-Deoxyserratinine

(2011) Houhua Li et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Short, Enantioselective Total Syntheses of (−)-8-Demethoxyrunanine and (−)-Cepharatines A, C, and D

(2011) Kangway V. Chuang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Quaternary centres bearing nitrogen (α-tertiary amines) as products of molecular rearrangements

(2011) Jonathan Clayden et al.   CHEMICAL COMMUNICATIONS

Huperzine A as Potential Treatment of Alzheimer's Disease: An Assessment on Chemistry, Pharmacology, and Clinical Studies

(2011) Giang T. Ha et al.   CHEMISTRY & BIODIVERSITY

Total Synthesis of (±)-Maistemonine, (±)-Stemonamide, and (±)-Isomaistemonine

(2011) Zhi-Hua Chen et al.   JOURNAL OF ORGANIC CHEMISTRY

Application of the Helquist Annulation inLycopodiumAlkaloid Synthesis: Unified Total Syntheses of (−)-8-Deoxyserratinine, (+)-Fawcettimine, and (+)-Lycoflexine

(2011) Yu-Rong Yang et al.   JOURNAL OF ORGANIC CHEMISTRY

Total Synthesis ofN-Methylwelwitindolinone D Isonitrile

(2011) Vikram Bhat et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of Gelsemoxonine

(2011) Jun Shimokawa et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (−)-N-Methylwelwitindolinone C Isothiocyanate

(2011) Alexander D. Huters et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of (−)-N-Methylwelwitindolinone C Isothiocyanate, (−)-N-Methylwelwitindolinone C Isonitrile, and (−)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate

(2011) Kevin M. Allan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of Oxidized Welwitindolinones and (−)-N-Methylwelwitindolinone C Isonitrile

(2011) Kyle W. Quasdorf et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The Chemical Synthesis of Tetrodoxin: An Ongoing Quest

(2011) Jaclyn Chau et al.   Marine Drugs

Synthesis of manzacidin A and C: efficient construction of quaternary carbon stereocenters bearing nitrogen substituents

(2011) Yoshiyasu Ichikawa et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Total Synthesis of (−)-Histrionicotoxin

(2011) Yohei Adachi et al.   ORGANIC LETTERS

Total Synthesis of (±)-Cylindricine C

(2011) Guillaume Lapointe et al.   ORGANIC LETTERS

Asymmetric Total Synthesis of Clavolonine

(2011) Kenji Nakahara et al.   ORGANIC LETTERS

Total Synthesis of (−)-Salinosporamide A

(2011) Nobuhiro Satoh et al.   ORGANIC LETTERS

Total synthesis of (±)-isophellibiline

(2011) Raymond L. Funk et al.   TETRAHEDRON LETTERS

A robust and scalable synthesis of the potent neuroprotective agent (−)-huperzine A

(2011) Maung Kyaw Moe Tun et al.   Chemical Science

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

(2011) Kangway V. Chuang et al.   Chemical Science

Total synthesis of (±)-maistemonine and (±)-stemonamide

(2010) Zhi-Hua Chen et al.   CHEMICAL COMMUNICATIONS

Total Synthesis of (−)-Salinosporamide A

(2010) Yuji Kaiya et al.   Chemistry-An Asian Journal

Concise Total Synthesis of (±)-Lycodine

(2010) Chihiro Tsukano et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

An Enantio- and Diastereocontrolled Synthesis of (–)-Salinosporamide A

(2010) Yoshiharu Iwabuchi et al.   HETEROCYCLES

Development of an Enantioselective Route toward theLycopodiumAlkaloids: Total Synthesis of Lycopodine

(2010) Hua Yang et al.   JOURNAL OF ORGANIC CHEMISTRY

Total Synthesis of (+)-Nankakurines A and B and (±)-5-epi-Nankakurine A

(2010) Ryan A. Altman et al.   JOURNAL OF ORGANIC CHEMISTRY

Bioinspired Total Synthesis and Human Proteasome Inhibitory Activity of (−)-Salinosporamide A, (−)-Homosalinosporamide A, and Derivatives Obtained via Organonucleophile Promoted Bis-cyclizations

(2010) Henry Nguyen et al.   JOURNAL OF ORGANIC CHEMISTRY

Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization

(2010) Daniel F. Fischer et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (+)-Fastigiatine

(2010) Brian B. Liau et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Scalable Total Syntheses ofN-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F

(2010) Timothy Newhouse et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The chemistry of Stemona alkaloids: An update

(2010) Ronaldo Aloise Pilli et al.   NATURAL PRODUCT REPORTS

Total Synthesis of (−)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction

(2010) Yu-Rong Yang et al.   ORGANIC LETTERS

Concise Synthesis of theErythrinaAlkaloid 3-Demethoxyerythratidinone via Combined Rhodium Catalysis

(2010) Jung Min Joo et al.   ORGANIC LETTERS

Asymmetric Synthesis of Substituted Homotropinones fromN-Sulfinyl β-Amino Ketone Ketals. (−)-Euphococcinine and (−)-Adaline

(2010) Franklin A. Davis et al.   ORGANIC LETTERS

Synthesis and Absolute Structure of Manzacidin B

(2010) Tetsuro Shinada et al.   ORGANIC LETTERS

Synthesis of the optically active key intermediate of FR901483

(2010) Shigeru Ieda et al.   TETRAHEDRON LETTERS

The Lycopodium Alkaloids

(2009) Hiroshi Morita et al.   HETEROCYCLES

Formal Syntheses of (±)-Stemonamine and (±)-Cephalotaxine

(2009) Yu-Ming Zhao et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective Total Synthesis of (−)-Acutumine

(2009) Fang Li et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereoselective Synthesis of (+)-Euphococcinine and (−)-Adaline

(2009) Mélissa Arbour et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereoselective Synthesis of (+)-Aspidofractinine

(2009) David Gagnon et al.   JOURNAL OF ORGANIC CHEMISTRY

Biomimetic Total Synthesis of (±)-8-Oxoerymelanthine

(2009) Yuki Yoshida et al.   JOURNAL OF ORGANIC CHEMISTRY

Organometallic Enantiomeric Scaffolding. Sequential Semipinacol/1,5-“Michael-like” Reactions as a Strategic Approach to Bridgehead-Quaternary Center Aza[3.3.1]Bicyclics: Application to the Total Synthesis of (−)-Adaline

(2009) Thomas C. Coombs et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (−)-Acutumine

(2009) Fang Li et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (−)-Himandrine

(2009) Mohammad Movassaghi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantiospecific Total Syntheses of Kapakahines B and F

(2009) Timothy Newhouse et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

New approaches for the synthesis of erythrinan alkaloids

(2009) Fengzhi Zhang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Concise Synthesis of the Bicyclic Scaffold ofN-Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization

(2009) Xia Tian et al.   ORGANIC LETTERS

Total Synthesis of (−)-Huperzine A

(2009) Takahiro Koshiba et al.   ORGANIC LETTERS

Concise Total Syntheses of theLycopodiumAlkaloids (±)-Nankakurines A and B via Luciduline

(2009) Xiayun Cheng et al.   ORGANIC LETTERS

Total synthesis of (−)-amathaspiramide F

(2009) Kazuhiko Sakaguchi et al.   TETRAHEDRON

Entry to Heterocycles Based on Indium-Catalyzed Conia-Ene Reactions: Asymmetric Synthesis of (−)-Salinosporamide A

(2008) Keisuske Takahashi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis of AntiproliferativeCephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

(2008) Joseph D. Eckelbarger et al.   CHEMISTRY-A EUROPEAN JOURNAL

Enantioselective Total Syntheses of Omuralide, 7-epi-Omuralide, and (+)-Lactacystin

(2008) Christopher J. Hayes et al.   JOURNAL OF ORGANIC CHEMISTRY

A Second Generation Formal Synthesis of (−)-Cephalotaxine

(2008) Abdul Hameed et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of Isohasubanan Alkaloids via Enantioselective Ketone Allylation and Discovery of an Unexpected Rearrangement

(2008) Daniel K. Nielsen et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective Total Syntheses of Nankakurines A and B: Confirmation of Structure and Establishment of Absolute Configuration

(2008) Bradley L. Nilsson et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Total Synthesis of (±)-Psychotrimine

(2008) Timothy Newhouse et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Total Synthesis of Lycopodine

(2008) Hua Yang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A concise and straightforward total synthesis of (±)-salinosporamide A, based on a biosynthesis model

(2008) Nicholas P Mulholland et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

An Efficient Total Synthesis of (±)-Stemonamine

(2008) Yu-Ming Zhao et al.   ORGANIC LETTERS

Utilization of a Michael Addition: Dipolar Cycloaddition Cascade for the Synthesis of (±)-Cylindricine C

(2008) Andrew C. Flick et al.   ORGANIC LETTERS

Total Synthesis of Salinosporamide A

(2008) Takeo Fukuda et al.   ORGANIC LETTERS

Short Synthesis of (−)-Cephalotaxine Using a Radical Cascade

(2008) Tsuyoshi Taniguchi et al.   ORGANIC LETTERS

An Efficient Asymmetric Synthesis of Manzacidin C

(2008) Kristy Tran et al.   ORGANIC LETTERS

Total synthesis of (±)-stemonamide, (±)-isostemonamide, (±)-stemonamine, and (±)-isostemonamine using a radical cascade

(2008) Tsuyoshi Taniguchi et al.   TETRAHEDRON

Short and stereoselective synthesis of manzacidins A and C, and their enantiomers

(2008) Kentaro Oe et al.   TETRAHEDRON LETTERS

Total Synthesis of (±)-Stemonamide and (±)-Isostemonamide Using a Radical Cascade

(2007) Tsuyoshi Taniguchi et al.   ORGANIC LETTERS