Cargando…

Total synthesis of the indolizidine alkaloid tashiromine

BACKGROUND: Tashiromine (1) is a naturally occurring indolizidine alkaloid. It has been the subject of thirteen successful total syntheses to date. Our own approach centres on the stereoselective construction of the indolizidine core by capture of an electrophilic acyliminium species by a pendant al...

Descripción completa

Detalles Bibliográficos
Autores principales:	Marsden, Stephen P, McElhinney, Alison D
Formato:	Texto
Lenguaje:	English
Publicado:	Beilstein-Institut 2008
Materias:	Full Research Paper
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2241604/ https://www.ncbi.nlm.nih.gov/pubmed/18221553 http://dx.doi.org/10.1186/1860-5397-4-8

Ejemplares similares

Synthesis of the Benzo-fused Indolizidine Alkaloid Mimics
por: Comins, Daniel L, et al.
Publicado: (2007)

Knorr-Rabe partial reduction of pyrroles: Application to the synthesis of indolizidine alkaloids
por: Gourlay, Brendon S, et al.
Publicado: (2008)

Novel stereocontrolled syntheses of tashiromine and epitashiromine
por: Kiss, Loránd, et al.
Publicado: (2015)

New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates
por: Riley, Darren L, et al.
Publicado: (2016)

Synthesis of (–)-Indolizidine 167B based on domino hydroformylation/cyclization reactions
por: Guazzelli, Giuditta, et al.
Publicado: (2008)

Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
por: Nelson, Angela, et al.
Publicado: (2008)

Flexible synthetic routes to poison-frog alkaloids of the 5,8-disubstituted indolizidine-class I: synthesis of common lactam chiral building blocks and application to the synthesis of (-)-203A, (-)-205A, and (-)-219F
por: Toyooka, Naoki, et al.
Publicado: (2007)

Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones
por: Bonanni, Marco, et al.
Publicado: (2007)

Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol
por: Michael, Joseph P, et al.
Publicado: (2008)

Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
por: Yayik, Nihan, et al.
Publicado: (2021)

Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors
por: Kobayashi, Soushi, et al.
Publicado: (2007)

A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids
por: Remuson, Roland
Publicado: (2007)

Crepidtumines A and B, Two Novel Indolizidine Alkaloids from Dendrobium crepidatum
por: Xu, Xiaolin, et al.
Publicado: (2020)

Unique indolizidine alkaloid securinine is a promising scaffold for the development of neuroprotective and antitumor drugs
por: Klochkov, Sergey, et al.
Publicado: (2021)

Pd-catalysed [3 + 3] annelations in the stereoselective synthesis of indolizidines
por: Provoost, Olivier Y, et al.
Publicado: (2007)

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
por: Nishiyama, Takashi, et al.
Publicado: (2021)

Indolizidines and quinolizidines: natural products and beyond
por: Michael, Joseph P
Publicado: (2007)

Production of Therapeutically Relevant Indolizidine Alkaloids in Securinega suffruticosa In Vitro Shoots Maintained in Liquid Culture Systems
por: Raj, Danuta, et al.
Publicado: (2014)

Crepidatumines C and D, Two New Indolizidine Alkaloids from Dendrobium crepidatum Lindl. ex Paxt.
por: Xu, Xiaolin, et al.
Publicado: (2019)

Catalytic enantioselective reductive alkynylation of amides enables one-pot syntheses of pyrrolidine, piperidine and indolizidine alkaloids
por: Xu, Fang-Fang, et al.
Publicado: (2023)

Two-directional synthesis as a tool for diversity-oriented synthesis: Synthesis of alkaloid scaffolds
por: O’Connell, Kieron M G, et al.
Publicado: (2012)

Aminomethylation/hydrogenolysis as an alternative to direct methylation of metalated isoquinolines – a novel total synthesis of the alkaloid 7-hydroxy-6-methoxy-1-methylisoquinoline
por: Melzer, Benedikt C, et al.
Publicado: (2018)

Synthesis of New Indolizidine Derivatives from 1-(2-Quinolyl)-2-propen-1-ol
por: Giomi, Donatella, et al.
Publicado: (2018)

Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes
por: Marsden, Stephen P, et al.
Publicado: (2005)

Total synthesis of (±)-coerulescine and (±)-horsfiline
por: Kulkarni, Mukund G, et al.
Publicado: (2010)

Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
por: Despiau, Carole F, et al.
Publicado: (2014)

Total synthesis of ochnaflavone
por: Ndoile, Monica M, et al.
Publicado: (2013)

Total synthesis of decarboxyaltenusin
por: Warmuth, Lucas, et al.
Publicado: (2021)

Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis
por: Gerasyuto, Aleksey I, et al.
Publicado: (2013)

Total Synthesis of the Akuammiline Alkaloid Picrinine
por: Smith, Joel M., et al.
Publicado: (2014)

Total Synthesis of Alkaloid 205B
por: Tsukanov, Sergey V., et al.
Publicado: (2014)

Total Synthesis of Dimeric HPI Alkaloids
por: Shen, Xianfu, et al.
Publicado: (2016)

Health literacy practices in 3D social virtual world
por: McElhinney, E
Publicado: (2023)

Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A
por: Chaubet, Guilhem, et al.
Publicado: (2017)

Total Synthesis and Bioactivity Mapping of Geodiamolide H
por: Nasufović, Veselin, et al.
Publicado: (2021)

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin
por: Wildermuth, Raphael E., et al.
Publicado: (2021)

Enantioselective total synthesis of (R)-(−)-complanine
por: Kamanos, Krystal A D, et al.
Publicado: (2012)

P(4)O(10)/TfOH mediated domino condensation–cyclization of amines with diacids: a route to indolizidine alkaloids under catalyst- and solvent-free conditions
por: Mandrekar, Ketan S., et al.
Publicado: (2022)

Synthesis of skeletally diverse alkaloid-like molecules: exploitation of metathesis substrates assembled from triplets of building blocks
por: Maurya, Sushil K, et al.
Publicado: (2013)

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids
por: Warskulat, Anne‐Christin, et al.
Publicado: (2016)

Cannot write session to /tmp/vufind_sessions/sess_0tsjad4t0vfistm3n6759mlknp