Literature DB >> 20161278

Synthetic Studies Towards the Mitomycins: Construction of the Tetracyclic Core via a Reductive Aminocyclization Reaction.

Daniel A Gubler1, Robert M Williams.   

Abstract

The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the 8-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein.

Entities:  

Year:  2009        PMID： 20161278      PMCID： PMC2702872          DOI： 10.1016/j.tetlet.2009.05.004

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

1.  DNA Cross-Linking Agents as Antitumor Drugs.

Authors:  Scott R. Rajski; Robert M. Williams
Journal:  Chem Rev       Date:  1998-12-17       Impact factor: 60.622

2.  Concise enantioselective synthesis of (+)-FR66979 and (+)-FR900482: dimethyldioxirane-mediated construction of the hydroxylamine hemiketal.

Authors:  Ted C Judd; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2002-12-16       Impact factor: 15.336

3.  A MOLECULAR MECHANISM OF MITOMYCIN ACTION: LINKING OF COMPLEMENTARY DNA STRANDS.

Authors:  V N IYER; W SZYBALSKI
Journal:  Proc Natl Acad Sci U S A       Date:  1963-08       Impact factor: 11.205

4.  Mitomycin, a new antibiotic from Streptomyces. I.

Authors:  T HATA; T HOSHI; K KANAMORI; A MATSUMAE; Y SANO; T SHIMA; R SUGAWARA
Journal:  J Antibiot (Tokyo)       Date:  1956-07       Impact factor: 2.649

5.  A concise total synthesis of (+)-FR900482 and (+)-FR66979.

Authors:  Ted C Judd; Robert M Williams
Journal:  J Org Chem       Date:  2004-04-16       Impact factor: 4.354

Review 6.  Mitomycin C: a clinical update.

Authors:  W T Bradner
Journal:  Cancer Treat Rev       Date:  2001-02       Impact factor: 12.111

Review 7.  Synthetic studies on heterocyclic natural products.

Authors:  Marco A Ciufolini
Journal:  Farmaco       Date:  2005-08

8.  Synthetic and biosynthetic studies on FR900482 and mitomycin C: an efficient and stereoselective hydroxymethylation of an advanced benzazocane intermediate.

Authors:  Hidenori Namiki; Stephen Chamberland; Daniel A Gubler; Robert M Williams
Journal:  Org Lett       Date:  2007-11-30       Impact factor: 6.005
  8 in total

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