Literature DB >> 23899273

A convergent total synthesis of the potent cephalostatin/ritterazine hybrid -25-epi ritterostatin GN1N.

Ananda Kumar Kanduluru1, Prabal Banerjee, John A Beutler, Philip L Fuchs.   

Abstract

The convergent synthesis of 25-epi ritterostatin GN1N is described for the first time, starting from hecogenin acetate (HA). Stereoselective dihydroxylation employing the chiral ligand (DHQ)2PHAL was used as the key step to introduce the C25 epi-stereocenter on the north 1 segment. The title compound was obtained through a coupling reaction between the C3-keto-azide (cstat North 1) and North G.

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Year:  2013        PMID： 23899273      PMCID： PMC7511990          DOI： 10.1021/jo401171q

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


  16 in total

Review 1.  Chemistry of trisdecacyclic pyrazine antineoplastics: the cephalostatins and ritterazines.

Authors:  Seongmin Lee; Thomas G LaCour; Philip L Fuchs
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

2.  A practical synthesis of cephalostatin 1.

Authors:  Yong Shi; Lanqi Jia; Qing Xiao; Quan Lan; Xiaohu Tang; Dahai Wang; Min Li; Yu Ji; Tao Zhou; Weisheng Tian
Journal:  Chem Asian J       Date:  2011-02-16

3.  Natural products reveal cancer cell dependence on oxysterol-binding proteins.

Authors:  Anthony W G Burgett; Thomas B Poulsen; Kittikhun Wangkanont; D Ryan Anderson; Chikako Kikuchi; Kousei Shimada; Shuichi Okubo; Kevin C Fortner; Yoshihiro Mimaki; Minpei Kuroda; Jason P Murphy; David J Schwalb; Eugene C Petrella; Ivan Cornella-Taracido; Markus Schirle; John A Tallarico; Matthew D Shair
Journal:  Nat Chem Biol       Date:  2011-08-07       Impact factor: 15.040

4.  Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid.

Authors:  Kanduluru Ananda Kumar; James J La Clair; Philip L Fuchs
Journal:  Org Lett       Date:  2011-09-14       Impact factor: 6.005

Review 5.  Targeting apoptosis pathways by natural compounds in cancer: marine compounds as lead structures and chemical tools for cancer therapy.

Authors:  Karin von Schwarzenberg; Angelika M Vollmar
Journal:  Cancer Lett       Date:  2010-07-31       Impact factor: 8.679

6.  A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7.

Authors:  Jong Seok Lee; Philip L Fuchs
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

7.  Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues.

Authors:  Wei Li; Thomas G LaCour; P L Fuchs
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

8.  Enantioselective synthesis of (+)-cephalostatin 1.

Authors:  Kevin C Fortner; Darryl Kato; Yoshiki Tanaka; Matthew D Shair
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419

Review 9.  Cephalostatin analogues--synthesis and biological activity.

Authors:  Timo Flessner; Rolf Jautelat; Ulrich Scholz; Ekkehard Winterfeldt
Journal:  Fortschr Chem Org Naturst       Date:  2004

Review 10.  Review of cytotoxic cephalostatins and ritterazines: isolation and synthesis.

Authors:  Bryan R Moser
Journal:  J Nat Prod       Date:  2008-01-15       Impact factor: 4.050
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  3 in total

1.  Ritterostatin GN 1N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.

Authors:  Andrew J Ambrose; Evelyne A Santos; Paula C Jimenez; Danilo D Rocha; Diego V Wilke; Paolo Beuzer; Josh Axelrod; Ananda Kumar Kanduluru; Philip L Fuchs; Hu Cang; Letícia V Costa-Lotufo; Eli Chapman; James J La Clair
Journal:  Chembiochem       Date:  2017-02-02       Impact factor: 3.164

Review 2.  Recent Advances in Drug Discovery from South African Marine Invertebrates.

Authors:  Michael T Davies-Coleman; Clinton G L Veale
Journal:  Mar Drugs       Date:  2015-10-14       Impact factor: 5.118

3.  Antitumor agent 25-epi Ritterostatin GN1N induces endoplasmic reticulum stress and autophagy mediated cell death in melanoma cells.

Authors:  Kausar Begam Riaz Ahmed; Ananda Kumar Kanduluru; Li Feng; Philip L Fuchs; Peng Huang
Journal:  Int J Oncol       Date:  2017-04-03       Impact factor: 5.650
  3 in total

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