Literature DB >> 24633775

Mechanistic aspects of the lycopodine Michael-Claisen domino cyclization.

Wilhelm A Eger1, Ernst Anders, Craig M Williams.   

Abstract

The Michael-Claisen domino (MCD) cyclization used in the lycopodine synthesis by Stork, was evaluated mechanistically using DFT calculations. Calculations suggest that a dianion is not formed, which conforms to classical dianion formation normally requiring strong kinetic bases. Instead ethoxide in ethanol produces a monoanionic species driving the MCD cyclization. This endeavor has opened up potential to expand the scope of this unique reaction and provide educational clarity.

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Year:  2014        PMID： 24633775     DOI： 10.1007/s00894-014-2173-0

Source DB:  PubMed          Journal:  J Mol Model        ISSN： 0948-5023            Impact factor:   1.810


  4 in total

1.  Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model.

Authors:  Maurizio Cossi; Nadia Rega; Giovanni Scalmani; Vincenzo Barone
Journal:  J Comput Chem       Date:  2003-04-30       Impact factor: 3.376

2.  The stereospecific total synthesis of dl-lycopodine.

Authors:  G Stork; R A Kretchmer; R H Schlessinger
Journal:  J Am Chem Soc       Date:  1968-03-13       Impact factor: 15.419

3.  Revisiting [3 + 3] route to 1,3-cyclohexanedione frameworks: hidden aspect of thermodynamically controlled enolates.

Authors:  T Ishikawa; R Kadoya; M Arai; H Takahashi; Y Kaisi; T Mizuta; K Yoshikai; S Saito
Journal:  J Org Chem       Date:  2001-11-30       Impact factor: 4.354

4.  Domino double Michael-Claisen cyclizations: a powerful general tool for introducing quaternary stereocenters at C4 of cyclohexane-1,3-diones and total synthesis of diverse families of sterically congested alkaloids.

Authors:  Teruhiko Ishikawa; Kazuhiro Kudo; Ken Kuroyabu; Satoshi Uchida; Takayuki Kudoh; Seiki Saito
Journal:  J Org Chem       Date:  2008-09-10       Impact factor: 4.354
  4 in total

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