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Literature DB >> 19235818

Total synthesis of cribrostatin 6.

Abstract

Fast and furious: Cribrostatin 6, an antimicrobial and antineoplastic agent, was the target of a total synthesis where the longest linear sequence was only four steps. The key step involves a tandem 4pi electrocyclic ring opening, radical cyclization, and homolytic aromatic substitution sequence to afford the tricyclic core of the natural product.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2009 PMID： 19235818 PMCID： PMC2790822 DOI： 10.1002/anie.200806269

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

7 in total

1. Identification of potent water soluble purine-scaffold inhibitors of the heat shock protein 90.

Authors: Huazhong He; Danuta Zatorska; Joungnam Kim; Julia Aguirre; Laura Llauger; Yuhong She; Nian Wu; Robert M Immormino; Daniel T Gewirth; Gabriela Chiosis
Journal: J Med Chem Date: 2006-01-12 Impact factor: 7.446

2. Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins.

Authors: Sanzhong Luo; Xueling Mi; Long Zhang; Song Liu; Hui Xu; Jin-Pei Cheng
Journal: Angew Chem Int Ed Engl Date: 2006-05-05 Impact factor: 15.336

3. Synthesis and stereochemical assignment of FR252921, a promising immunosuppressant.

Authors: J Russell Falck; Anyu He; Hiroki Fukui; Hideyuki Tsutsui; Akella Radha
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Synthesis of cribrostatin 6.

Authors: Michael D Markey; T Ross Kelly
Journal: J Org Chem Date: 2008-08-30 Impact factor: 4.354

5. Efficient Synthesis of 1,4-Dihydro-2H-isoquinoline-3,5,8-triones via Cyclobutene Ring Expansion.

Authors: Peter Wipf; Corey R. Hopkins
Journal: J Org Chem Date: 1999-09-03 Impact factor: 4.354

6. Antineoplastic agents. 485. Isolation and structure of cribrostatin 6, a dark blue cancer cell growth inhibitor from the marine sponge Cribrochalina sp.

Authors: George R Pettit; Jeremiah C Collins; John C Knight; Delbert L Herald; Ronald A Nieman; Michael D Williams; Robin K Pettit
Journal: J Nat Prod Date: 2003-04 Impact factor: 4.050

7. Antibacterial activity of the marine sponge constituent cribrostatin 6.

Authors: Robin K Pettit; Bridget R Fakoury; John C Knight; Christine A Weber; George R Pettit; Gary D Cage; Sandy Pon
Journal: J Med Microbiol Date: 2004-01 Impact factor: 2.472

7 in total

8 in total

Total synthesis of cribrostatin 6.

1. Identification of potent water soluble purine-scaffold inhibitors of the heat shock protein 90.

2. Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins.

3. Synthesis and stereochemical assignment of FR252921, a promising immunosuppressant.

4. Synthesis of cribrostatin 6.

5. Efficient Synthesis of 1,4-Dihydro-2H-isoquinoline-3,5,8-triones via Cyclobutene Ring Expansion.

6. Antineoplastic agents. 485. Isolation and structure of cribrostatin 6, a dark blue cancer cell growth inhibitor from the marine sponge Cribrochalina sp.

7. Antibacterial activity of the marine sponge constituent cribrostatin 6.

1. Total Synthesis of the Aglycone of IB-00208.

2. General and expedient synthesis of 1,4-dioxygenated xanthones.

3. Asymmetric synthesis of ageliferin.

4. Tandem Electrocyclic Ring Opening/Radical Cyclization: Application to the Total Synthesis of Cribrostatin 6.

5. Concise Approach to 1,4-Dioxygenated Xanthones via Novel Application of the Moore Rearrangement.

6. Cribrostatin 6 induces death in cancer cells through a reactive oxygen species (ROS)-mediated mechanism.

7. Approaches to polycyclic 1,4-dioxygenated xanthones. Application to total synthesis of the aglycone of IB-00208.

8. The synthesis of imidazo[1,5-a]quinolines via a decarboxylative cyclization under metal-free conditions.