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Literature DB >> 16555834

Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.

Abstract

Diels-Alder cycloaddition of 10 followed by Wittig homologation and intramolecular diene cyclozirconation of the resulting triene under equilibrating conditions led to the tricyclic 6-6-5 ketone 5 with high diastereocontrol. The derived alpha-azido ketone 16 cyclized efficiently to the heptacyclic pyrazine core of ritterazine N.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16555834 PMCID： PMC3248823 DOI： 10.1021/jo052656m

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

7 in total

1. Stereoselective synthesis of structurally simplified cephalostatin analogues by multiple Heck reactions and their biological evaluation.

Authors: Lutz F Tietze; Wolf-Rüdiger Krahnert
Journal: Chemistry Date: 2002-05-03 Impact factor: 5.236

2. Isolation of 13 New Ritterazines from the Tunicate Ritterella tokioka and Chemical Transformation of Ritterazine B(1).

Authors: Seketsu Fukuzawa; Shigeki Matsunaga; Nobuhiro Fusetani
Journal: J Org Chem Date: 1997-06-27 Impact factor: 4.354

3. Cephalostatin 1 inactivates Bcl-2 by hyperphosphorylation independent of M-phase arrest and DNA damage.

Authors: Irina M Müller; Verena M Dirsch; Anita Rudy; Nancy López-Antón; George R Pettit; Angelika M Vollmar
Journal: Mol Pharmacol Date: 2005-02-09 Impact factor: 4.436

4. An efficient synthesis of the C-23 deoxy, 17 alpha-hydroxy South 1 hemisphere and its cephalostatin 1 analog.

Authors: Wei Li; Philip L Fuchs
Journal: Org Lett Date: 2003-08-07 Impact factor: 6.005

5. Cephalostatin 1 selectively triggers the release of Smac/DIABLO and subsequent apoptosis that is characterized by an increased density of the mitochondrial matrix.

Authors: Verena M Dirsch; Irina M Müller; Sören T Eichhorst; George R Pettit; Yoshiaki Kamano; Masuo Inoue; Jun-Ping Xu; Yoshitatsu Ichihara; Gerhard Wanner; Angelika M Vollmar
Journal: Cancer Res Date: 2003-12-15 Impact factor: 12.701

6. Ritterazine B, a new cytotoxic natural compound, induces apoptosis in cancer cells.

Authors: Takefumi Komiya; Nobuhiro Fusetani; Shigeki Matsunaga; Akihito Kubo; Frederic J Kaye; Michael J Kelley; Kenji Tamura; Makoto Yoshida; Masahiro Fukuoka; Kazuhiko Nakagawa
Journal: Cancer Chemother Pharmacol Date: 2003-01-14 Impact factor: 3.333

7. Antineoplastic agents. 398. Isolation and structure elucidation of cephalostatins 18 and 19.

Authors: G R Pettit; R Tan; J Xu; Y Ichihara; M D Williams; M R Boyd
Journal: J Nat Prod Date: 1998-07 Impact factor: 4.050

7 in total

5 in total

Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.

1. Stereoselective synthesis of structurally simplified cephalostatin analogues by multiple Heck reactions and their biological evaluation.

2. Isolation of 13 New Ritterazines from the Tunicate Ritterella tokioka and Chemical Transformation of Ritterazine B(1).

3. Cephalostatin 1 inactivates Bcl-2 by hyperphosphorylation independent of M-phase arrest and DNA damage.

4. An efficient synthesis of the C-23 deoxy, 17 alpha-hydroxy South 1 hemisphere and its cephalostatin 1 analog.

5. Cephalostatin 1 selectively triggers the release of Smac/DIABLO and subsequent apoptosis that is characterized by an increased density of the mitochondrial matrix.

6. Ritterazine B, a new cytotoxic natural compound, induces apoptosis in cancer cells.

7. Antineoplastic agents. 398. Isolation and structure elucidation of cephalostatins 18 and 19.

1. Preparation of the 5/5-spiroketal of the ritterazines.

Review 2. Chemistry of trisdecacyclic pyrazine antineoplastics: the cephalostatins and ritterazines.

3. Importance of a 4-Alkyl Substituent for Activity in the Englerin Series.

4. Construction of the tricyclic A-B-C core of the Veratrum alkaloids.

5. Synthesis of C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 via "red-ox" modifications of hecogenin acetate.