Literature DB >> 19617925

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

Yu Zhang1, Aleksey I Gerasyuto, Quincy A Long, Richard P Hsung.   

Abstract

The first success in constructing a member of quinolizidine family of alkaloids employing an intramolecular aza-[3 + 3] annulation strategy is described here. The key feature is the usage of vinylogous urethane tethered to a vinyl iminium intermediate with trifluoroacetate serving as the counter anion. The proof-of-concept is illustrated with the synthesis of 2-deoxy-lasubine II.

Entities:  

Year:  2008        PMID： 19617925      PMCID： PMC2711553          DOI： 10.1055/s-0028-1087661

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  33 in total

1.  A [3 + 3] annelation approach to tetrahydropyridines.

Authors:  Lisa C Pattenden; Robert A J Wybrow; Stephen A Smith; Joseph P A Harrity
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

2.  Alkaloid synthesis using chiral delta-amino beta-ketoesters: a stereoselective synthesis of (-)-lasubine II.

Authors:  F A Davis; B Chao
Journal:  Org Lett       Date:  2000-08-24       Impact factor: 6.005

3.  Highly stereoselective formal

Authors: 
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

4.  Synthesis of (--)-lasubine(I) via a planar chiral [(eta6-arene)Cr(CO)3] complex.

Authors:  H Ratni; E P Kündig
Journal:  Org Lett       Date:  1999-12-16       Impact factor: 6.005

5.  Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation.

Authors:  Steven J O'Malley; Kian L Tan; Anja Watzke; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2005-10-05       Impact factor: 15.419

6.  Synthesis of the quinolizidine alkaloids (-)-lasubine II and (+/-)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones.

Authors:  Thomas G Back; Michael D Hamilton; Vania J J Lim; Masood Parvez
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

7.  A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones.

Authors:  Michael J McLaughlin; Richard P Hsung; Kevin P Cole; Juliet M Hahn; Jiashi Wang
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

8.  Total syntheses of enantiomerically enriched R-(+)- and S-(-)-deplancheine.

Authors:  Nadiya Sydorenko; Craig A Zificsak; Aleksey I Gerasyuto; Richard P Hsung
Journal:  Org Biomol Chem       Date:  2005-04-25       Impact factor: 3.876

9.  A concise total synthesis of (-)-cylindricine C through a stereoselective intramolecular aza-[3 + 3] annulation strategy.

Authors:  Jacob J Swidorski; Jiashi Wang; Richard P Hsung
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

10.  Intramolecular formal aza-[3 + 3] cycloaddition approach to indoloquinolizidine alkaloids. A stereoselective total synthesis of (+/-)-tangutorine.

Authors:  Shengjun Luo; Craig A Zificsak; Richard P Hsung
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  4 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.  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
  4 in total

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