55254-30-3Relevant academic research and scientific papers
A two-directional synthesis of (+/-)-perhydrohistrionicotoxin.
Stockman, Robert A,Sinclair, Alex,Arini, Louise G,Szeto, Peter,Hughes, David L
, p. 1598 - 1602 (2007/10/03)
An entirely two-directional synthesis of (+/-)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (+/-)-histrionicotoxin and (+/-)-histrionicotoxin 235A.
A Novel and Highly Stereoselective Approach to Aza-Spirocycles. A Short Total Synthesis of 2-epi-(±)-Perhydrohistrionicotoxin and an Unprecedented Decarboxylation of 2-Pyrones
McLaughlin, Michael J.,Hsung, Richard P.,Cole, Kevin P.,Hahn, Juliet M.,Wang, Jiashi
, p. 2017 - 2020 (2007/10/03)
(Matrix Presented) A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(±)-perhydrohistrionicotoxin with high diastereomeric contro
Highly Stereoselective Ring Contraction of Heterocyclic Enamines: Total Synthesis of Perhydrohistrionicotoxin and Its 2,6-Epimer
Duhamel, Pierre,Kotera, Mitsuharu,Monteil, Thierry,Marabout, Benoit,Davoust, Daniel
, p. 4419 - 4425 (2007/10/02)
The total syntheses of perhydrohistrionicotoxin (PHTX) and its 2,6-epimer in which the pentyl group, introduced in the early stages, controls the relative configuration of C6 in a highly stereoselective manner are described.Seven-membered heterocyclic ena
THE STEREOCHEMISTRY OF SPIROPIPERIDINE CYCLIZATIONS (HISTRIONICOTOXIN, PART I)
Glanzmann, Michael,Karalai, Chatchanok,Ostersehlt, Bernd,Schoen, Uwe,Frese, Christiane,Winterfeldt, Ekkehard
, p. 2805 - 2810 (2007/10/02)
The spirocyclization of straight-chain triketo-intermediates, similar to possible biogenetic precursors of histrionicotoxin, is shown to be stereoselective, generating the non-natural configuration at C-2.Aiming at an sp2-center in this positio
