Literature DB >> 19404485

Asymmetric Synthesis of (+)-Iso-6-Cassine via Stereoselective Intramolecular Amidomercuration.

Satwinder Singh1, Om V Singh, Hyunsoo Han.   

Abstract

The first asymmetric synthesis of (+)-iso-6-cassine is described. Lipase-catalyzed resolution, enantioselective Overman rearrangement, and diastereoselective intramolecular amidomercuration were used for the installation of the three stereocenters in (+)-iso-6-cassine, and cross-metathesis was employed for the attachment of the side-chain.

Entities:  

Year:  2007        PMID： 19404485      PMCID： PMC2674249          DOI： 10.1016/j.tetlet.2007.09.129

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  25 in total

1.  Improved Conditions for Facile Overman Rearrangement(1).

Authors:  Toshio Nishikawa; Masanori Asai; Norio Ohyabu; Minoru Isobe
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

Review 2.  Indolizidine and quinolizidine alkaloids.

Authors:  J P Michael
Journal:  Nat Prod Rep       Date:  2001-10       Impact factor: 13.423

3.  An expeditious stereoselective synthesis of natural (-)-Cassine via cascade HWE [3 + 2]-cycloaddition process.

Authors:  Claus Herdeis; Patrick Küpper; Sophie Plé
Journal:  Org Biomol Chem       Date:  2005-12-21       Impact factor: 3.876

4.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

5.  Formation of bicyclic ethers from Lewis acid promoted cyclizations of cyclic oxonium ions.

Authors:  Pradip K Sasmal; Martin E Maier
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

6.  2-Piperidone Type of Chiral Building Block for 3-Piperidinol Alkaloid Synthesis.

Authors:  Naoki Toyooka; Yasuko Yoshida; Yasuhito Yotsui; Takefumi Momose
Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

7.  Lepadins F-H, new cis-decahydroquinoline alkaloids from the Australian ascidian Aplidium tabascum.

Authors:  Rohan A Davis; Anthony R Carroll; Ronald J Quinn
Journal:  J Nat Prod       Date:  2002-04       Impact factor: 4.050

8.  Tandem overman rearrangement and intramolecular amidomercuration reactions. stereocontrolled synthesis of cis- and trans-2,6-dialkylpiperidines.

Authors:  Om V Singh; Hyunsoo Han
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

9.  Catalytic asymmetric rearrangement of allylic N-aryl trifluoroacetimidates. A useful method for transforming prochiral allylic alcohols to chiral allylic amines.

Authors:  Larry E Overman; Carolyn E Owen; Mary M Pavan; Christopher J Richards
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

10.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419
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  1 in total

1.  A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.

Authors:  Dustin J Covell; M Christina White
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457
  1 in total

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