Literature DB >> 15012070

Stereoselective synthesis of the ABC ring system of norzoanthamine.

Subhash Ghosh1, Fatima Rivas, Derek Fischer, Miguel A González, Emmanuel A Theodorakis.   

Abstract

[reaction: see text] An efficient synthesis of enone 4, representing the ABC ring motif of norzoanthamine, is presented. The crucial C22 quaternary center was introduced via a stereoselective methylation of enone 8. The trans-anti-trans relative configuration of the ABC framework of 4 was installed via a sequence of reactions that included a hydroboration and a modified Robinson annulation.

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Year:  2004        PMID： 15012070     DOI： 10.1021/ol036492c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Enantioselective total synthesis of (-)-jiadifenolide.

Authors:  Jing Xu; Lynnie Trzoss; Weng K Chang; Emmanuel A Theodorakis
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2.  Enantioselective synthesis of (-)-jiadifenin, a potent neurotrophic modulator.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

3.  Enantioselective synthesis of the ABC ring motif of norzoanthamine based on asymmetric Robinson annulation reactions.

Authors:  Thong X Nguyen; Marianna Dakanali; Lynnie Trzoss; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2011-05-26       Impact factor: 6.005

4.  Intramolecular Cyclization Strategies Toward the Synthesis of Zoanthamine Alkaloids.

Authors:  Derek Fischer; Thong X Nguyen; Lynnie Trzoss; Marianna Dakanali; Emmanuel A Theodorakis
Journal:  Tetrahedron Lett       Date:  2011-09-21       Impact factor: 2.415

5.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2013-03-22       Impact factor: 5.236

6.  Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

Authors:  Michelle H Lacoske; Jing Xu; Noel Mansour; Chao Gao; Emmanuel A Theodorakis
Journal:  Org Chem Front       Date:  2015-04-01       Impact factor: 5.281

7.  Toosendanin: synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II).

Authors:  Yuya Nakai; Sabine Pellett; William H Tepp; Eric A Johnson; Kim D Janda
Journal:  Bioorg Med Chem       Date:  2009-12-22       Impact factor: 3.641

8.  Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Beilstein J Org Chem       Date:  2013-06-12       Impact factor: 2.883
  8 in total

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