Journal ArticleDOI
Palladium catalyzed reductive cyclization reaction in alkaloid synthesis :an enantioselective total synthetic route to (+)-pumiliotoxin c
Reads0
Chats0
TLDR
In this paper, an enantioselective total synthetic route to (+)-pumiliotoxin C (1) has been described, using the chirally homogeneous cyclohexenol 3.About:
This article is published in Tetrahedron Letters.The article was published on 1996-06-17. It has received 18 citations till now. The article focuses on the topics: Enantioselective synthesis & Palladium.read more
Citations
More filters
Journal ArticleDOI
Quinoline, quinazoline and acridone alkaloids
TL;DR: This review covers the isolation, structure determination, synthesis and biological activity of quinoline, quinazoline and acridone alkaloids from plant, microbial and animal sources.
Journal ArticleDOI
Study on radical amidation onto aromatic rings with (diacyloxyiodo)arenes
TL;DR: In this article, sulfonamides of primary amines bearing an aromatic ring at the γ-position were treated with diacyloxyiodo arenes and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields.
Book ChapterDOI
Chapter One - Alkaloids from Amphibian Skins
Journal ArticleDOI
The asymmetric synthesis of (-)-pumiliotoxin C using tandem catalysis *
Ewold W. Dijk,Lavinia Panella,Pedro Pinho,Robert Naasz,Auke Meetsma,Adriaan J. Minnaard,Ben L. Feringa +6 more
TL;DR: In this paper, the potent neurotoxin (−)-pumiliotoxin C has been prepared in 8 steps starting from 2-cyclohexenone, where the key steps are a tandem asymmetric conjugate addition-allylic substitution reaction and a tandem Heck-alic substitution reaction.
Journal ArticleDOI
Enantioselective Synthesis of (−)-Pumiliotoxin C from a Chiral Amino Ester and an Acetylenic Sulfone that Acts as an Alkene Dipole Equivalent
TL;DR: In this paper, a new synthesis of the naturally occurring (−)-enantiomer of the dendrobatid alkaloid pumiliotoxin C (1) was achieved by the conjugate addition of methyl (−)-cis-2-amino-trans-6-methylcyclohexanecarboxylate (3) to 1-(p-toluenesulfonyl)-1-pentyne (4), followed by intramolecular acylation to afford (4aS,5R,8aR)-4a
References
More filters
Journal ArticleDOI
Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way
TL;DR: The ability of transition metal complexes to preorganize π-electron systems serves as the basis both of simple additions usually accompanied by subsequent hydrogen shifts and of cycloadditions as mentioned in this paper.
BookDOI
Alkaloids : chemical and biological perspectives
TL;DR: In this paper, the total synthesis of amaryllidaceae alkaloids has been studied using radical cyclization reactions in total syntheses of naturally occurring indole alkaloid.
Journal ArticleDOI
Efficacious modification of the mitsunobu reaction for inversions of sterically hindered secondary alcohols
TL;DR: In this article, a modification of the Mitsunobu protocol for effecting stereochemical inversions of alcohols has been discovered in which use of p-nitrobenzoic acid as the nucleophilic partner results in significantly improved yields with relatively hindered substrates.
Journal ArticleDOI
Organoaluminum-promoted Beckmann rearrangement of oxime sulfonates
Keiji Maruoka,Tohru Miyazaki,Mamoru Ando,Yasushi Matsumura,Soichi Sakane,Kazunobu Hattori,Hisashi Yamamoto +6 more
Journal ArticleDOI
Ruthenium-catalyzed hydration of nitriles and transformation of .delta.-keto nitriles to ene-lactams
TL;DR: In this article, the RuH 2 (PPh 3 ) 4 catalyst was used for the short-step synthesis of (-)-pumiliotoxin C. The effectiveness of the reaction was illustrated by the short step synthesis of PUMILOTE C.
Related Papers (5)
Ruthenium-catalyzed hydration of nitriles and transformation of δ-ketonitriles to ene-lactams: total synthesis of (−)-pumiliotoxin C
An enantioselective synthesis and the absolute configuration of natural pumiliotoxin‐C. Preliminary communication
Wolfgang Oppolzer,Elmar Flaskamp +1 more