Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
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Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function propertiesBiomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.Cycloadditions of noncomplementary substituted 1,2,3-triazines.Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope10'-Fluorovinblastine and 10'-Fluorovincristine: Synthesis of a Key Series of Modified Vinca Alkaloids.Total synthesis of (-)-kopsinine and ent-(+)-kopsinineIron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of novel 20'-vinblastine analoguesDivergent total syntheses of (-)-aspidospermine and (+)-spegazzinine.Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine SynthesisNew insights into the mechanism and an expanded scope of the Fe(III)-mediated vinblastine coupling reaction.Total Synthesis of (-)-Vindoline and (+)-4-epi-Vindoline Based on a 1,3,4-Oxadiazole Tandem Intramolecular [4 + 2]/[3 + 2] Cycloaddition Cascade Initiated by an Allene Dienophile.Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20' urea derivatives.Total synthesis of kopsinine.Synthesis of spirocyclic indolines by interruption of the Bischler-Napieralski reaction.Potent Vinblastine C20' Ureas Displaying Additionally Improved Activity Against a Vinblastine-Resistant Cancer Cell Line.Transannular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles: total synthesis of a unique set of vinblastine analogues.Total synthesis of a key series of vinblastines modified at C4 that define the importance and surprising trends in activity.Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance.Application of the aza-Diels-Alder reaction in the synthesis of natural products.Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.Synthesis of a Potent Vinblastine: Rationally Designed Added Benign Complexity.Polyhydroxylated pyrrolizidine alkaloids from transannular iodoaminations: application to the asymmetric syntheses of (-)-hyacinthacine A1, (-)-7a-epi-hyacinthacine A1, (-)-hyacinthacine A2, and (-)-1-epi-alexine.Palladium(0)-catalyzed intramolecular dearomative arylation of pyrroles.Enantioselective cycloaddition of carbonyl ylides with arylallenes using Rh2(S-TCPTTL)4.The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.Brønsted Acid-Catalyzed Tandem Cyclizations of Tryptamine-Ynamides Yielding 1H-Pyrrolo[2,3-d]carbazole Derivatives.Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis.Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.Total Synthesis of (-)-Vindorosine.High expression of class III β-tubulin has no impact on functional cancer cell growth inhibition of a series of key vinblastine analogs.Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides.Ni(ClO4)(2)-catalysed regio- and diastereoselective [3+2] cycloaddition of indoles and aryl oxiranyl-dicarboxylates/diketones: a facile access to furo[3,4-b]indoles.Highly Efficient Formal [2+2+2] Strategy for the Rapid Construction of Polycyclic Spiroindolines: A Concise Synthesis of 11-Demethoxy-16-epi-myrtoidine.Domino intramolecular Diels-Alder reactions to construct a 6/6/5/5 fused tetracyclic framework.Key analogs of a uniquely potent synthetic vinblastine that contain modifications of the C20' ethyl substituent.
P2860
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P2860
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
description
2010 nî lūn-bûn
@nan
2010 թուականի Սեպտեմբերին հրատարակուած գիտական յօդուած
@hyw
2010 թվականի սեպտեմբերին հրատարակված գիտական հոդված
@hy
2010年の論文
@ja
2010年論文
@yue
2010年論文
@zh-hant
2010年論文
@zh-hk
2010年論文
@zh-mo
2010年論文
@zh-tw
2010年论文
@wuu
name
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@ast
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@en
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@nl
type
label
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@ast
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@en
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@nl
prefLabel
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@ast
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@en
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@nl
P2093
P2860
P356
P1476
Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
@en
P2093
Daisuke Kato
Dale L Boger
Yoshikazu Sasaki
P2860
P304
13533-13544
P356
10.1021/JA106284S
P407
P577
2010-09-01T00:00:00Z