Literature DB >> 30443158

Asymmetric Syntheses of Potent Antitumor Macrolides Cryptophycin B and Arenastatin A.

Arun K Ghosh1, A Bischoff1.   

Abstract

Efficient and highly stereoselective syntheses of cryptophycin B and arenastatin A, potent cytotoxic agents, are described. An ester-derived titanium enolate mediated syn-aldol reaction was employed to generate the stereocenters C-5 and C-6. The route is convergent and provides a convenient access to the synthesis of structural variants of cryptophycins as well as members of its family.

Entities:  

Keywords:  Aldols; Arenastatin A; Asymmetric synthesis; Cryptophycins; Natural products

Year:  2004        PMID： 30443158      PMCID： PMC6233905          DOI： 10.1002/ejoc.200300814

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  26 in total

1.  Synthesis of cryptophycin 52 using the sharpless asymmetric dihydroxylation: diol to epoxide transformation optimized for a base-sensitive substrate.

Authors:  J Liang; E D Moher; R E Moore; D W Hoard
Journal:  J Org Chem       Date:  2000-05-19       Impact factor: 4.354

2.  Enantiospecific Total Synthesis of the Potent Antitumor Macrolides Cryptophycins 1 and 8.

Authors:  Kevin M. Gardinier; James W. Leahy
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

3.  Stereospecific synthesis of cryptophycin 1.

Authors:  Lian-Hai Li; Marcus A Tius
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

4.  Halohydrin analogues of cryptophycin 1: synthesis and biological activity.

Authors:  G I Georg; S M Ali; V J Stella; W N Waugh; R H Himes
Journal:  Bioorg Med Chem Lett       Date:  1998-08-04       Impact factor: 2.823

5.  Interaction of cryptophycin 1 with tubulin and microtubules.

Authors:  K Kerksiek; M R Mejillano; R E Schwartz; G I Georg; R H Himes
Journal:  FEBS Lett       Date:  1995-12-11       Impact factor: 4.124

6.  Three new cryptophycins from Nostoc sp. GSV 224.

Authors:  G V Subbaraju; T Golakoti; G M Patterson; R E Moore
Journal:  J Nat Prod       Date:  1997-03       Impact factor: 4.050

7.  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

8.  Enantioselective synthesis of a 3'-dephenylcryptophycin synthon.

Authors:  M J Eggen; G I Georg
Journal:  Bioorg Med Chem Lett       Date:  1998-11-17       Impact factor: 2.823

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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