Literature DB >> 15844916

Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach.

Amos B Smith1, B Scott Freeze, Ming Xian, Tomoyasu Hirose.   

Abstract

[structure: see text] A highly convergent, fourth-generation total synthesis of (+)-discodermolide (1), with a longest linear sequence of 17 steps and an overall yield of 9.0%, has been achieved. Highlighting the strategy is the efficient construction and sequential, bidirectional union of a linchpin comprising the C(9)-C(14) Wittig salt-vinyl iodide (-)-18. Importantly, Wittig salt generation proceeded in excellent yield under ambient pressure.

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Year:  2005        PMID: 15844916     DOI: 10.1021/ol050455z

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


  11 in total

1.  (+)-Discodermolide: Total Synthesis, Construction of Novel Analogues, and Biological Evaluation.

Authors:  Amos B Smith; B Scott Freeze
Journal:  Tetrahedron       Date:  2007-01-07       Impact factor: 2.457

2.  Potentiation of taxol efficacy and by discodermolide in ovarian carcinoma xenograft-bearing mice.

Authors:  Gloria S Huang; Lluis Lopez-Barcons; B Scott Freeze; Amos B Smith; Gary L Goldberg; Susan Band Horwitz; Hayley M McDaid
Journal:  Clin Cancer Res       Date:  2006-01-01       Impact factor: 12.531

3.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

Review 4.  Advances in exploring the therapeutic potential of marine natural products.

Authors:  Xiao Liang; Danmeng Luo; Hendrik Luesch
Journal:  Pharmacol Res       Date:  2019-07-25       Impact factor: 7.658

5.  Highly concentrated catalytic asymmetric allylation of ketones.

Authors:  Alfred J Wooten; Jeung Gon Kim; Patrick J Walsh
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

6.  Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.

Authors:  Zhiyong Yu; Robert J Ely; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

7.  Design, synthesis and biological evaluation of a simplified fluorescently labeled discodermolide as a molecular probe to study the binding of discodermolide to tubulin.

Authors:  Jun Qi; Adam R Blanden; Susan Bane; David G I Kingston
Journal:  Bioorg Med Chem       Date:  2011-07-02       Impact factor: 3.641

8.  Design and synthesis of (+)-discodermolide-paclitaxel hybrids leading to enhanced biological activity.

Authors:  Amos B Smith; Keizo Sugasawa; Onur Atasoylu; Chia-Ping Huang Yang; Susan Band Horwitz
Journal:  J Med Chem       Date:  2011-08-26       Impact factor: 7.446

9.  A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Authors:  Qiuzhe Xie; Richard W Denton; Kathlyn A Parker
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

10.  High content screening of diverse compound libraries identifies potent modulators of tubulin dynamics.

Authors:  Luca Laraia; Jamie Stokes; Amy Emery; Grahame J McKenzie; Ashok R Venkitaraman; David R Spring
Journal:  ACS Med Chem Lett       Date:  2014-02-24       Impact factor: 4.345

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