Literature DB >> 15563138

Total synthesis of (-)-disorazole C1.

Peter Wipf1, Thomas H Graham.   

Abstract

The antimitotic natural product disorazole C1 was isolated in 1994 from the fermentation broth of the myxobacterium Sorangium cellulosum. We have developed a highly convergent and stereoselective total synthesis of this compound which establishes its relative and absolute configuration. Key features of our synthesis include a highly convergent strategy and selective functional group manipulations that minimize decomposition of the sensitive polyene macrodiolide.

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Year:  2004        PMID: 15563138     DOI: 10.1021/ja0443068

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


  14 in total

1.  Assignment of absolute configuration to SCH 351448 via total synthesis.

Authors:  Lael L Cheung; Shinji Marumoto; Christopher D Anderson; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-06-11       Impact factor: 6.005

2.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       Impact factor: 15.419

3.  Total synthesis of (-)-CP2-disorazole C1.

Authors:  Chad D Hopkins; John C Schmitz; Edward Chu; Peter Wipf
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

4.  Total synthesis of iejimalide B.

Authors:  Qingshou Chen; Dirk Schweitzer; John Kane; V Jo Davisson; Paul Helquist
Journal:  J Org Chem       Date:  2011-04-20       Impact factor: 4.354

5.  Identifying a resistance determinant for the antimitotic natural products disorazole C1 and A1.

Authors:  John S Lazo; Celeste E Reese; Andreas Vogt; Laura L Vollmer; Carolyn A Kitchens; Eckhard Günther; Thomas H Graham; Chad D Hopkins; Peter Wipf
Journal:  J Pharmacol Exp Ther       Date:  2009-12-15       Impact factor: 4.030

6.  Mitotic slippage in non-cancer cells induced by a microtubule disruptor, disorazole C1.

Authors:  Fengfeng L Xu; Youssef Rbaibi; Kirill Kiselyov; John S Lazo; Peter Wipf; William S Saunders
Journal:  BMC Chem Biol       Date:  2010-02-11

Review 7.  Isolation, biology and chemistry of the disorazoles: new anti-cancer macrodiolides.

Authors:  Chad D Hopkins; Peter Wipf
Journal:  Nat Prod Rep       Date:  2009-03-11       Impact factor: 13.423

8.  Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors:  Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

9.  Microtubule binding and disruption and induction of premature senescence by disorazole C(1).

Authors:  Marni Brisson Tierno; Carolyn A Kitchens; Bethany Petrik; Thomas H Graham; Peter Wipf; Fengfeng L Xu; William S Saunders; Brianne S Raccor; Raghavan Balachandran; Billy W Day; Jane R Stout; Claire E Walczak; Alexander P Ducruet; Celeste E Reese; John S Lazo
Journal:  J Pharmacol Exp Ther       Date:  2008-12-09       Impact factor: 4.030

10.  Self-Assembly of Disorazole C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.

Authors:  Kevin J Ralston; H Clinton Ramstadius; Richard C Brewster; Helen S Niblock; Alison N Hulme
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-29       Impact factor: 15.336

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