Literature DB >> 23116136

Total synthesis of aeruginosin 98B.

Barry M Trost1, Toshiyuki Kaneko, Neil G Andersen, Christoph Tappertzhofen, Bruce Fahr.   

Abstract

The first total synthesis of aeruginosin 98B was accomplished. The key step is a highly diastereoselective Pd-catalyzed intramolecular asymmetric allylic alkylation reaction of a diastereomeric mixture of allylic carbonates that is enabled by the use of racemic phosphine ligand L1.

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Year:  2012        PMID： 23116136      PMCID： PMC3551629          DOI： 10.1021/ja309947n

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


  17 in total

1.  Total synthesis and stereochemical revision of (+)-aeruginosin 298-A.

Authors:  P Wipf; J L Methot
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

2.  Cyanopeptide analogues: new lead structures for the design and synthesis of new thrombin inhibitors.

Authors:  G Radau; J Stürzebecher
Journal:  Pharmazie       Date:  2002-11       Impact factor: 1.267

3.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.

Authors:  Takashi Ohshima; Vijay Gnanadesikan; Tomoyuki Shibuguchi; Yuhei Fukuta; Tetsuhiro Nemoto; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

5.  Chemistry and biology of the aeruginosin family of serine protease inhibitors.

Authors:  Karolina Ersmark; Juan R Del Valle; Stephen Hanessian
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Solid-phase combinatorial synthesis of aeruginosin derivatives and their biological evaluation.

Authors:  Takayuki Doi; Yoichiro Hoshina; Hiroyuki Mogi; Yoshifumi Yamada; Takashi Takahashi
Journal:  J Comb Chem       Date:  2006 Jul-Aug

7.  New methods for side-chain protection of cysteine.

Authors:  C W West; M A Estiarte; D H Rich
Journal:  Org Lett       Date:  2001-04-19       Impact factor: 6.005

8.  Total synthesis and structural revision of the presumed aeruginosins 205A and B.

Authors:  Stephen Hanessian; Xiaotian Wang; Karolina Ersmark; Juan R Del Valle; Ellen Klegraf
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

9.  The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin.

Authors:  Stephen Hanessian; Martin Tremblay; Jens F W Petersen
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419

10.  Structure-based organic synthesis of unnatural aeruginosin hybrids as potent inhibitors of thrombin.

Authors:  Stephen Hanessian; Karolina Ersmark; Xiaotian Wang; Juan R Del Valle; Niklas Blomberg; Yafeng Xue; Ola Fjellström
Journal:  Bioorg Med Chem Lett       Date:  2007-03-27       Impact factor: 2.823
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  2 in total

1.  Enantioselective construction of cis-hydroindole scaffolds via an asymmetric inverse-electron-demand Diels-Alder reaction: application to the formal total synthesis of (+)-minovincine.

Authors:  Fangqing Zhang; Bing-Tao Ren; Yuqiao Zhou; Yangbin Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2022-04-15       Impact factor: 9.969

2.  A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products.

Authors:  Christopher E Malmberg; Stephen Chamberland
Journal:  J Vis Exp       Date:  2016-09-09       Impact factor: 1.355
  2 in total

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