Literature DB >> 17002353

A concise total synthesis of DL-histrionicotoxin.

Maheswaran S Karatholuvhu1, Alex Sinclair, Annabella F Newton, Marie-Lyne Alcaraz, Robert A Stockman, Philip L Fuchs.   

Abstract

The synthesis of (+/-)-histrionicotoxin has been achieved in just nine steps using a two-directional synthesis strategy. Key reactions include a two-directional cross-metathesis, a tandem oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition cascade, a selective Z,Z-bisenyne formation, and a one-pot N-O and bischloroacetylene reduction.

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Year:  2006        PMID： 17002353     DOI： 10.1021/ja065015x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  5 in total

1.  A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

2.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

3.  Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy.

Authors:  Iain Coldham; Adam J M Burrell; Hélène D S Guerrand; Luke Watson; Nathaniel G Martin; Niall Oram
Journal:  Beilstein J Org Chem       Date:  2012-01-18       Impact factor: 2.883

4.  Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)2-catalyzed cycloisomerization and SmI2-induced ring expansion.

Authors:  Kunihiro Matsumura; Keisuke Nishikawa; Hiroaki Yoshida; Matsumi Doe; Yoshiki Morimoto
Journal:  RSC Adv       Date:  2018-03-21       Impact factor: 3.361

5.  Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.

Authors:  Annabella F Newton; Martin Rejzek; Marie-Lyne Alcaraz; Robert A Stockman
Journal:  Beilstein J Org Chem       Date:  2008-01-17       Impact factor: 2.883
  5 in total

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