Literature DB >> 18044909

Facile synthesis of naphthoquinone spiroketals by diastereoselective oxidative [3 + 2] cycloaddition.

Kun-Liang Wu1, Stephanie Wilkinson, Norbert O Reich, Thomas R R Pettus.   

Abstract

A highly selective oxidative [3 + 2] cycloaddition of chiral enol ethers and hydroxynaphthoquinone is described. This convergent strategy is amenable to an enantioselective synthesis of beta-rubromycin and related naphthoquinone spiroketals. Several compounds were found to inhibit DNA-polymerase and telomerase in a manner resembling alpha-rubromycin and beta-rubromycin.

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Year:  2007        PMID： 18044909      PMCID： PMC2430727          DOI： 10.1021/ol702450d

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


  16 in total

1.  Quantification of telomerase activity by direct scintillation counting.

Authors:  S Kazmer; K M Pan; L Vassilev
Journal:  J Biochem Biophys Methods       Date:  1999-08-12

2.  Mechanism of human telomerase inhibition by BIBR1532, a synthetic, non-nucleosidic drug candidate.

Authors:  Emanuelle Pascolo; Christian Wenz; Joachim Lingner; Norbert Hauel; Henning Priepke; Iris Kauffmann; Pilar Garin-Chesa; Wolfgang J Rettig; Klaus Damm; Andreas Schnapp
Journal:  J Biol Chem       Date:  2002-02-19       Impact factor: 5.157

3.  The Total Synthesis of Heliquinomycinone This work was supported by the National Institutes of Health (Grant numbers: AI 16943 and HL25848). The authors thank Dr. Makoto Chino of Nippon Kayaku Co., Ltd. for kindly providing a sample of heliquinomycin, and Yashuiro Itagaki of Columbia University for high-resolution mass spectral analyses.

Authors:  Tony Siu; Donghui Qin; Samuel J. Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

4.  Studies in the Total Synthesis of Heliquinomycinone: Proof of Concept and Assembly of a Fully Mature Spirocyclization Precursor This work was supported by the National Institutes of Health (Grant numbers: AI 16943 and HL25848). A Postdoctoral Fellowship is gratefully acknowledged by R.X.R. (NIH, Grant Number IF32EY06750-0181). The authors thank Dr. Daniel Chen for important initial experiments, Dr. Brian Bridgewater and Prof. Ged Parkin of Columbia University for X-ray crystal structure analysis of 11 a, and Yashuiro Itagaki for high-resolution mass spectral analyses.

Authors:  Donghui Qin; Rex X. Ren; Tony Siu; Changsheng Zheng; Samuel J. Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

5.  Inhibition of telomerase by BIBR 1532 and related analogues.

Authors:  D K Barma; Anissa Elayadi; J R Falck; David R Corey
Journal:  Bioorg Med Chem Lett       Date:  2003-04-07       Impact factor: 2.823

6.  Total synthesis of (+/-)-gamma-rubromycin on the basis of two aromatic Pummerer-type reactions.

Authors:  Shuji Akai; Keisuke Kakiguchi; Yuka Nakamura; Ikumi Kuriwaki; Toshifumi Dohi; Shusaku Harada; Ozora Kubo; Nobuyoshi Morita; Yasuyuki Kita
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  [Rubromycin II].

Authors:  H Brockmann; W Lenk; G Schwantje; A Zeeck
Journal:  Chem Ber       Date:  1969

8.  Synthesis of bisbenzannulated spiroketals-model studies for a modular approach to rubromycins.

Authors:  Sebastian Sörgel; Cengiz Azap; Hans-Ulrich Reissig
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

9.  [The structure of rubromycin].

Authors:  H Brockmann; W Lenk; G Schwantje; A Zeeck
Journal:  Tetrahedron Lett       Date:  1966-07       Impact factor: 2.415

10.  Specific association of human telomerase activity with immortal cells and cancer.

Authors:  N W Kim; M A Piatyszek; K R Prowse; C B Harley; M D West; P L Ho; G M Coviello; W E Wright; S L Weinrich; J W Shay
Journal:  Science       Date:  1994-12-23       Impact factor: 47.728
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  3 in total

1.  New strategies for natural products containing chroman spiroketals.

Authors:  Jason C Green; G Leslie Burnett; Thomas R R Pettus
Journal:  Pure Appl Chem       Date:  2012       Impact factor: 2.453

2.  Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.

Authors:  Guodong Liu; Jacqueline M Wurst; Derek S Tan
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

3.  Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

Authors:  Maurice A Marsini; Yaodong Huang; Christopher C Lindsey; Kun-Liang Wu; Thomas R R Pettus
Journal:  Org Lett       Date:  2008-03-13       Impact factor: 6.005
  3 in total

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