Literature DB >> 11804488

A convergent approach to cyclopeptide alkaloids: total synthesis of sanjoinine G1.

Taoues Temal-Laïb1, Jacqueline Chastanet, Jieping Zhu.   

Abstract

A general strategy for the synthesis of cyclopeptide alkaloids containing an endocyclic aryl-alkyl ether bond has been developed featuring a key intramolecular S(N)Ar reaction. The importance of the N-terminal protective group in the realization of such a strategy is documented. From the appropriate amino acid constituents, the natural sanjoinine G1, a 14-membered para cyclophane, has been synthesized in seven steps with 21% overall yield.

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Year:  2002        PMID: 11804488     DOI: 10.1021/ja0170807

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

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Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

3.  Build/couple/pair strategy for the synthesis of stereochemically diverse macrolactams via head-to-tail cyclization.

Authors:  Mark E Fitzgerald; Carol A Mulrooney; Jeremy R Duvall; Jingqiang Wei; Byung-Chul Suh; Lakshmi B Akella; Anita Vrcic; Lisa A Marcaurelle
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4.  Synthesis of a stereochemically diverse library of medium-sized lactams and sultams via S(N)Ar cycloetherification.

Authors:  Baudouin Gerard; Jeremy R Duvall; Jason T Lowe; Tiffanie Murillo; Jingqiang Wei; Lakshmi B Akella; Lisa A Marcaurelle
Journal:  ACS Comb Sci       Date:  2011-04-28       Impact factor: 3.784

5.  Synthesis of stereochemically and skeletally diverse fused ring systems from functionalized C-glycosides.

Authors:  Baudouin Gerard; Maurice D Lee; Sivaraman Dandapani; Jeremy R Duvall; Mark E Fitzgerald; Sarathy Kesavan; Jason T Lowe; Jean-Charles Marié; Bhaumik A Pandya; Byung-Chul Suh; Morgan Welzel O'Shea; Michael Dombrowski; Diane Hamann; Berenice Lemercier; Tiffanie Murillo; Lakshmi B Akella; Michael A Foley; Lisa A Marcaurelle
Journal:  J Org Chem       Date:  2013-05-21       Impact factor: 4.354

Review 6.  Selected synthetic strategies to cyclophanes.

Authors:  Mukesh Eknath Shirbhate; Gopalkrushna T Waghule; Sambasivarao Kotha
Journal:  Beilstein J Org Chem       Date:  2015-07-29       Impact factor: 2.883

7.  Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy.

Authors:  Jisun Lee; Madeleine M Joullié
Journal:  Chem Sci       Date:  2018-01-31       Impact factor: 9.825

8.  Modular, One-Pot, Sequential Aziridine Ring Opening-S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams.

Authors:  Joanna K Loh; Naeem Asad; Thiwanka B Samarakoon; Paul R Hanson
Journal:  J Org Chem       Date:  2015-10-08       Impact factor: 4.354

  8 in total

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