Literature DB >> 16734447

Total synthesis of (+)-yatakemycin.

Kentaro Okano1, Hidetoshi Tokuyama, Tohru Fukuyama.   

Abstract

A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene.

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Year:  2006        PMID: 16734447     DOI: 10.1021/ja0619455

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


  14 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.

Authors:  Mark S Tichenor; Karen S MacMillan; John D Trzupek; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2007-08-11       Impact factor: 15.419

3.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

4.  Annulated diketopiperazines from dipeptides or Schöllkopf reagents via tandem cyclization-intramolecular N-arylation.

Authors:  Hwan Jung Lim; Judith C Gallucci; T V RajanBabu
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

5.  Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer.

Authors:  Mark S Tichenor; John D Trzupek; David B Kastrinsky; Futoshi Shiga; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

Review 6.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors.

Authors:  Xiangyu Wu; Wei Hao; Ke-Yin Ye; Binyang Jiang; Gisselle Pombar; Zhidong Song; Song Lin
Journal:  J Am Chem Soc       Date:  2018-10-26       Impact factor: 15.419

Review 8.  Fukuyama reduction, Fukuyama coupling and Fukuyama-Mitsunobu alkylation: recent developments and synthetic applications.

Authors:  Sana Sikandar; Ameer Fawad Zahoor; Shazia Naheed; Bushra Parveen; Kulsoom Ghulam Ali; Rabia Akhtar
Journal:  Mol Divers       Date:  2021-02-11       Impact factor: 2.943

9.  Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids.

Authors:  Joerg H Schrittwieser; Verena Resch; Silvia Wallner; Wolf-Dieter Lienhart; Johann H Sattler; Jasmin Resch; Peter Macheroux; Wolfgang Kroutil
Journal:  J Org Chem       Date:  2011-07-19       Impact factor: 4.354

10.  Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions.

Authors:  Amberly B Sanford; Elizabeth R Jarvo
Journal:  Synlett       Date:  2020-11-27       Impact factor: 2.454

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