Literature DB >> 19216517

Antineoplastic agents. 571. Total synthesis of bacillistatin 2.

George R Pettit1, Shougang Hu, John C Knight, Jean-Charles Chapuis.   

Abstract

The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.

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Year:  2009        PMID： 19216517      PMCID： PMC2837129          DOI： 10.1021/np800607x

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  4 in total

1.  Investigation of the Yamaguchi esterification mechanism. Synthesis of a lux-s enzyme inhibitor using an improved esterification method.

Authors:  Ilirian Dhimitruka; John Santalucia
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

2.  An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: a powerful and convenient mixed anhydride method promoted by basic catalysts.

Authors:  Isamu Shiina; Mari Kubota; Hiromi Oshiumi; Minako Hashizume
Journal:  J Org Chem       Date:  2004-03-19       Impact factor: 4.354

3.  Antineoplastic agents. 570. Isolation and structure elucidation of bacillistatins 1 and 2 from a marine Bacillus silvestris.

Authors:  George R Pettit; John C Knight; Delbert L Herald; Robin K Pettit; Fiona Hogan; Venugopal J R V Mukku; John S Hamblin; Michael J Dodson; Jean-Charles Chapuis
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

4.  On the mechanisms of the formation of L-alloisoleucine and the 2-hydroxy-3-methylvaleric acid stereoisomers from L-isoleucine in maple syrup urine disease patients and in normal humans.

Authors:  O A Mamer; M L Reimer
Journal:  J Biol Chem       Date:  1992-11-05       Impact factor: 5.157
  4 in total
  4 in total

1.  Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control.

Authors:  Suzanne M Batiste; Jeffrey N Johnston
Journal:  Proc Natl Acad Sci U S A       Date:  2016-12-14       Impact factor: 11.205

Review 2.  Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.

Authors:  Ricardo Ribeiro; Eugénia Pinto; Carla Fernandes; Emília Sousa
Journal:  Mar Drugs       Date:  2022-06-15       Impact factor: 6.085

3.  An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards 'clickable' biodegradable polylactide.

Authors:  Quanxuan Zhang; Hong Ren; Gregory L Baker
Journal:  Beilstein J Org Chem       Date:  2014-06-17       Impact factor: 2.883

Review 4.  Cyclic Peptides for the Treatment of Cancers: A Review.

Authors:  Dalifa Ramadhani; Rani Maharani; Amirah Mohd Gazzali; Muchtaridi Muchtaridi
Journal:  Molecules       Date:  2022-07-11       Impact factor: 4.927
  4 in total

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