Literature DB >> 22617820

Efficient, divergent synthesis of cryptophycin unit A analogues.

Kyle L Bolduc1, Scott D Larsen, David H Sherman.   

Abstract

A flexible and divergent synthesis of cryptophycin unit A analogues is described. This method relies on iridium-catalysed stereo- and enantioselective crotylation and chemoselective one-pot oxidative olefination to access common intermediate . Heck, cross metathesis, and Suzuki-Miyaura reactions are illustrated for the generation of methyl ester unit A analogues .

Entities:  

Year:  2012        PMID： 22617820      PMCID： PMC3494784          DOI： 10.1039/c2cc32417b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  27 in total

Review 1.  Cryptophycins: a novel class of potent antimitotic antitumor depsipeptides.

Authors:  C Shih; B A Teicher
Journal:  Curr Pharm Des       Date:  2001-09       Impact factor: 3.116

2.  A stereoselective synthesis of (+)-herboxidiene/GEX1A.

Authors:  Arun K Ghosh; Jianfeng Li
Journal:  Org Lett       Date:  2010-12-02       Impact factor: 6.005

3.  Chemoenzymatic synthesis of cryptophycin/arenastatin natural products.

Authors:  Zachary Q Beck; Courtney C Aldrich; Nathan A Magarvey; Gunda I Georg; David H Sherman
Journal:  Biochemistry       Date:  2005-10-18       Impact factor: 3.162

4.  Biosynthetic characterization and chemoenzymatic assembly of the cryptophycins. Potent anticancer agents from cyanobionts.

Authors:  Nathan A Magarvey; Zachary Q Beck; Trimurtulu Golakoti; Yousong Ding; Udo Huber; Thomas K Hemscheidt; Dafna Abelson; Richard E Moore; David H Sherman
Journal:  ACS Chem Biol       Date:  2006-12-15       Impact factor: 5.100

5.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

6.  Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain.

Authors:  M Eggen; C J Mossman; S B Buck; S K Nair; L Bhat; S M Ali; E A Reiff; T C Boge; G I Georg
Journal:  J Org Chem       Date:  2000-11-17       Impact factor: 4.354

7.  Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Authors:  Timothy W Funk; Jon Efskind; Robert H Grubbs
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

8.  Total synthesis of platensimycin and related natural products.

Authors:  K C Nicolaou; Ang Li; David J Edmonds; G Scott Tria; Shelby P Ellery
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

9.  Cryptophycin: a new antimicrotubule agent active against drug-resistant cells.

Authors:  C D Smith; X Zhang; S L Mooberry; G M Patterson; R E Moore
Journal:  Cancer Res       Date:  1994-07-15       Impact factor: 12.701

10.  In vitro pharmacology of cryptophycin 52 (LY355703) in human tumor cell lines.

Authors:  M M Wagner; D C Paul; C Shih; M A Jordan; L Wilson; D C Williams
Journal:  Cancer Chemother Pharmacol       Date:  1999       Impact factor: 3.333
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  2 in total

1.  A Versatile Chemoenzymatic Synthesis for the Discovery of Potent Cryptophycin Analogs.

Authors:  Jennifer J Schmidt; Yogan Khatri; Scott I Brody; Catherine Zhu; Halina Pietraszkiewicz; Frederick A Valeriote; David H Sherman
Journal:  ACS Chem Biol       Date:  2020-02-03       Impact factor: 5.100

Review 2.  Stabilizing versus destabilizing the microtubules: a double-edge sword for an effective cancer treatment option?

Authors:  Daniele Fanale; Giuseppe Bronte; Francesco Passiglia; Valentina Calò; Marta Castiglia; Florinda Di Piazza; Nadia Barraco; Antonina Cangemi; Maria Teresa Catarella; Lavinia Insalaco; Angela Listì; Rossella Maragliano; Daniela Massihnia; Alessandro Perez; Francesca Toia; Giuseppe Cicero; Viviana Bazan
Journal:  Anal Cell Pathol (Amst)       Date:  2015-09-21       Impact factor: 2.916
  2 in total

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