Literature DB >> 15212512

A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

Kosuke Namba1, Hyuk-Sang Jun, Yoshito Kishi.   

Abstract

A simple device consisting of two ion-exchange columns, two alumina-based filters, and a pump (Figure 1) was assembled to form the C8-C14 polycyclic ring system present in the halichondrin B class of marine natural products. The effectiveness of this device was tested for three substrates. In each case, the desired polycyclic ketal 3, 5, or 7 was obtained almost quantitatively in a single operation.

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Year:  2004        PMID: 15212512     DOI: 10.1021/ja047826b

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


  8 in total

1.  A synthesis of the C1-C15 domain of the halichondrins.

Authors:  Katrina L Jackson; James A Henderson; Jonathan C Morris; Hajime Motoyoshi; Andrew J Phillips
Journal:  Tetrahedron Lett       Date:  2008-04-01       Impact factor: 2.415

2.  Effective Procedure for Selective Ammonolysis of Monosubstituted Oxiranes: Application to E7389 Synthesis.

Authors:  Yosuke Kaburagi; Yoshito Kishi
Journal:  Tetrahedron Lett       Date:  2007-12       Impact factor: 2.415

3.  A total synthesis of norhalichondrin B.

Authors:  Katrina L Jackson; James A Henderson; Hajime Motoyoshi; Andrew J Phillips
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

Authors:  Yosuke Kaburagi; Yoshito Kishi
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005

5.  Second generation synthesis of C27-C35 building block of E7389, a synthetic halichondrin analogue.

Authors:  Yu-Rong Yang; Dae-Shik Kim; Yoshito Kishi
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

6.  Attempts to improve the overall stereoselectivity of the Ireland-Claisen rearrangement.

Authors:  Chi-Li Chen; Kosuke Namba; Yoshito Kishi
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

7.  Iron complexation to oxygen rich marine natural products: a computational study.

Authors:  Thomas J Manning; Jimmy Williams; Joey Jarrard; Teresa Gorman
Journal:  Mar Drugs       Date:  2010-01-04       Impact factor: 5.118

Review 8.  Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.

Authors:  Erika A Crane; Karl Gademann
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

  8 in total

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