Literature DB >> 26096055

Total Synthesis and Structural Revision of Antibiotic CJ-16,264.

K C Nicolaou1, Akshay A Shah2, Henry Korman3, Tabrez Khan4, Lei Shi2, Wisuttaya Worawalai3, Emmanuel A Theodorakis3.   

Abstract

The total synthesis and structural revision of antibiotic CJ-16,264 is described. Starting with citronellal, the quest for the target molecule featured a novel bis-transannular Diels-Alder reaction that casted stereoselectively the decalin system and included the synthesis of six isomers before demystification of its true structure.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  antibiotic; natural products; structural revision; total synthesis; transannular Diels-Alder reaction

Mesh：

Substances：

Year:  2015        PMID： 26096055      PMCID： PMC4530996          DOI： 10.1002/anie.201504337

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  14 in total

1.  New pyrrolizidinone antibiotics CJ-16,264 and CJ-16,367.

Authors:  Y Sugie; H Hirai; H Kachi-Tonai; Y J Kim; Y Kojima; Y Shiomi; A Sugiura; A Sugiura; Y Suzuki; N Yoshikawa; L Brennan; J Duignan; L H Huang; J Sutcliffe; N Kojima
Journal:  J Antibiot (Tokyo)       Date:  2001-11       Impact factor: 2.649

2.  UCS1025A and B, new antitumor antibiotics from the fungus Acremonium species.

Authors:  Tsutomu Agatsuma; Tsutomu Akama; Shinji Nara; Shigeki Matsumiya; Ryuichiro Nakai; Harumi Ogawa; Shizuo Otaki; Shun-Ichi Ikeda; Yutaka Saitoh; Yutaka Kanda
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

3.  Total synthesis of UCS1025A.

Authors:  Tristan H Lambert; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

Review 4.  Macrolactonizations in the total synthesis of natural products.

Authors:  A Parenty; X Moreau; J-M Campagne
Journal:  Chem Rev       Date:  2006-03       Impact factor: 60.622

5.  Efficient synthesis and resolution of pyrrolizidines.

Authors:  Renata Marcia de Figueiredo; Roland Fröhlich; Mathias Christmann
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 6.  The Diels--Alder reaction in total synthesis.

Authors:  K C Nicolaou; Scott A Snyder; Tamsyn Montagnon; Georgios Vassilikogiannakis
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

Review 7.  Recent applications of intramolecular Diels-Alder reactions to natural product synthesis.

Authors:  Martin Juhl; David Tanner
Journal:  Chem Soc Rev       Date:  2009-07-29       Impact factor: 54.564

8.  Stereocontrolled total synthesis of (+)-UCS1025A.

Authors:  Kenji Uchida; Takahiro Ogawa; Yoshinori Yasuda; Hiraku Mimura; Teppei Fujimoto; Tohru Fukuyama; Toshiyuki Wakimoto; Tomohiro Asakawa; Yoshitaka Hamashima; Toshiyuki Kan
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-09       Impact factor: 15.336

9.  Pyrrolizilactone, a new pyrrolizidinone metabolite produced by a fungus.

Authors:  Toshihiko Nogawa; Makoto Kawatani; Masakazu Uramoto; Akiko Okano; Harumi Aono; Yushi Futamura; Hiroyuki Koshino; Shunji Takahashi; Hiroyuki Osada
Journal:  J Antibiot (Tokyo)       Date:  2013-05-29       Impact factor: 2.649

10.  Comparative Diels-Alder reactivities within a family of valence bond isomers: a biomimetic total synthesis of (+/-)-UCS1025A.

Authors:  Thomas R Hoye; Vadims Dvornikovs
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419
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  5 in total

1.  Experimental Evolution of Diverse Strains as a Method for the Determination of Biochemical Mechanisms of Action for Novel Pyrrolizidinone Antibiotics.

Authors:  Kathryn Beabout; Megan D McCurry; Heer Mehta; Akshay A Shah; Kiran Kumar Pulukuri; Stephan Rigol; Yanping Wang; K C Nicolaou; Yousif Shamoo
Journal:  ACS Infect Dis       Date:  2017-09-27       Impact factor: 5.084

Review 2.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649

3.  Genome Mining and Assembly-Line Biosynthesis of the UCS1025A Pyrrolizidinone Family of Fungal Alkaloids.

Authors:  Li Li; Man-Cheng Tang; Shoubin Tang; Shushan Gao; Sameh Soliman; Leibniz Hang; Wei Xu; Tao Ye; Kenji Watanabe; Yi Tang
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

4.  Enantioselective Total Synthesis of Antibiotic CJ-16,264, Synthesis and Biological Evaluation of Designed Analogues, and Discovery of Highly Potent and Simpler Antibacterial Agents.

Authors:  K C Nicolaou; Kiran Kumar Pulukuri; Stephan Rigol; Marek Buchman; Akshay A Shah; Nicholas Cen; Megan D McCurry; Kathryn Beabout; Yousif Shamoo
Journal:  J Am Chem Soc       Date:  2017-10-24       Impact factor: 15.419

5.  Yuccalechins A-C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities.

Authors:  Łukasz Pecio; Mostafa Alilou; Ilkay Erdogan Orhan; Gokcen Eren; Fatma Sezer Senol Deniz; Hermann Stuppner; Wiesław Oleszek
Journal:  Molecules       Date:  2019-11-16       Impact factor: 4.411
  5 in total

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