Literature DB >> 20839833

Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.

Ken S Feldman1, Ahmed Yimam Nuriye.   

Abstract

A pentacyclic model system featuring the trans azabicyclo[3.3.0]octane unit of dibromopalau'amine was prepared with complete diastereoselectivity in the polycyclic core from a tricyclic precursor. The key transformations of this sequence include (a) a Pummerer reaction-mediated oxidative bicyclization, and (b) a Wolff rearrangement-based ring contraction to deliver the strained azabicyclo[3.3.0]octane core.

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Year:  2010        PMID： 20839833     DOI： 10.1021/ol1018322

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


  8 in total

1.  Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition.

Authors:  Kosuke Namba; Makto Inai; Uta Sundermeier; Thomas J Greshock; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2010-12-15       Impact factor: 2.415

2.  Asymmetric synthesis of ageliferin.

Authors:  Xiao Wang; Zhiqiang Ma; Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2011-09-08       Impact factor: 15.419

3.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica.

Authors:  E Paige Stout; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

4.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

Review 5.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

6.  Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.

Authors:  Manojkumar R Bhandari; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2011-02-21       Impact factor: 6.005

7.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

Review 8.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222
  8 in total

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