Literature DB >> 17338572

An intramolecular aza-[3+3] annulation approach to azaphenalene alkaloids. Total synthesis of myrrhine.

Aleksey I Gerasyuto1, Richard P Hsung.   

Abstract

A detailed account on the stereoselective total syntheses of azaphenalene alkaloids via an intramolecular aza-[3+3] annulation strategy is described here. All five members of the Coccinellidae family of defensive alkaloids were prepared from the same common intermediate, which was derived from a stereoselective aza-[3+3] annulation reaction.

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Year:  2007        PMID： 17338572     DOI： 10.1021/jo062533h

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  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

2.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

3.  Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

Authors:  Grant S Buchanan; Huifang Dai; Richard P Hsung; Aleksey I Gerasyuto; Casi M Scheinebeck
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

4.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

5.  Total synthesis of (+)-lepadin F.

Authors:  Gang Li; Richard P Hsung; Brian W Slafer; Irina K Sagamanova
Journal:  Org Lett       Date:  2008-09-27       Impact factor: 6.005

6.  A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.

Authors:  Yu Zhang; Aleksey I Gerasyuto; Quincy A Long; Richard P Hsung
Journal:  Synlett       Date:  2008-01-01       Impact factor: 2.454

7.  Two-directional synthesis as a tool for diversity-oriented synthesis: Synthesis of alkaloid scaffolds.

Authors:  Kieron M G O'Connell; Monica Díaz-Gavilán; Warren R J D Galloway; David R Spring
Journal:  Beilstein J Org Chem       Date:  2012-06-06       Impact factor: 2.883

8.  A strategy for complex dimer formation when biomimicry fails: total synthesis of ten coccinellid alkaloids.

Authors:  Trevor C Sherwood; Adam H Trotta; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2014-06-24       Impact factor: 15.419

9.  Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins.

Authors:  Brendan L Quigley; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-02       Impact factor: 9.825

10.  Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis.

Authors:  Aleksey I Gerasyuto; Zhi-Xiong Ma; Grant S Buchanan; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2013-06-18       Impact factor: 2.883
  10 in total

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