Literature DB >> 19928810

Toward tubulysin: gram-scale synthesis of tubuvaline-tubuphenylalanine fragment.

Srivari Chandrasekhar1, Bodugam Mahipal, Mitta Kavitha.   

Abstract

A practical and stereoselective synthesis of the tubuvaline-tubuphenylalanine (Tuv-Tup) fragment of tubulysin is achieved involving the opening of aziridine, crucial MacMillan alpha-hydroxylation on both fragments, and an epoxide-opening reaction.

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Year:  2009        PMID： 19928810     DOI： 10.1021/jo9015503

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Chemotherapeutic evaluation of a synthetic tubulysin analogue-dendrimer conjugate in c26 tumor bearing mice.

Authors:  William C Floyd; Gopal K Datta; Shinichi Imamura; Heidi M Kieler-Ferguson; Katherine Jerger; Andrew W Patterson; Megan E Fox; Francis C Szoka; Jean M J Fréchet; Jonathan A Ellman
Journal:  ChemMedChem       Date:  2011-01-03       Impact factor: 3.466

2.  Enantioselective homocrotylboration of aliphatic aldehydes.

Authors:  Hongkun Lin; Wenbo Pei; Hao Wang; Kendall N Houk; Isaac J Krauss
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

3.  Boron carboxylate catalysis of homoallylboration.

Authors:  Gabrielle J Dugas; Yu-hong Lam; K N Houk; Isaac J Krauss
Journal:  J Org Chem       Date:  2014-04-24       Impact factor: 4.354

4.  Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes.

Authors:  Jing Li; Alexander Preinfalk; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

5.  Diastereocontrol in Radical Addition to β-Benzyloxy Hydrazones: Revised Approach to Tubuvaline and Synthesis of O-Benzyltubulysin V Benzyl Ester.

Authors:  Manshu Li; Koushik Banerjee; Gregory K Friestad
Journal:  J Org Chem       Date:  2021-10-12       Impact factor: 4.354

6.  Stereoselective access to tubuphenylalanine and tubuvaline: improved Mn-mediated radical additions and assembly of a tubulysin tetrapeptide analog.

Authors:  Gregory K Friestad; Koushik Banerjee; Jean-Charles Marié; Umesh Mali; Lei Yao
Journal:  J Antibiot (Tokyo)       Date:  2016-02-17       Impact factor: 2.649
  6 in total

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