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Literature DB >> 17105273

Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1.

Abstract

The enantioselective total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C is reported. The approach involves tartrate-mediated, asymmetric nucleophilic epoxidation of a functionalized quinone monoketal to construct the highly substituted D-ring.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17105273 DOI： 10.1021/ja066621v

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

19 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Asymmetric total synthesis of the epoxykinamycin FL-120 B'.

Authors: Stephen S Scully; John A Porco
Journal: Angew Chem Int Ed Engl Date: 2011-08-30 Impact factor: 15.336

3. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

Authors: Seth B Herzon; Liang Lu; Christina M Woo; Shivajirao L Gholap
Journal: J Am Chem Soc Date: 2011-01-31 Impact factor: 15.419

4. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Authors: Hong Geun Lee; Jae Young Ahn; Amy S Lee; Matthew D Shair
Journal: Chemistry Date: 2010-11-22 Impact factor: 5.236

Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Asymmetric total synthesis of the epoxykinamycin FL-120 B'.

3. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

4. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Review 5. Recent advances in the chemistry and biology of naturally occurring antibiotics.

Review 6. Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Review 7. Diazo Compounds: Versatile Tools for Chemical Biology.

8. Cascade assembly of the benzo[a]anthraquinone ring system common to the angucycline antibiotics.

9. Direct C-H α-Arylation of Enones with ArI(O₂CR)₂ Reagents.

10. Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Asymmetric total synthesis of the epoxykinamycin FL-120 B'.

3. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

4. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Review 5. Recent advances in the chemistry and biology of naturally occurring antibiotics.

Review 6. Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Review 7. Diazo Compounds: Versatile Tools for Chemical Biology.

8. Cascade assembly of the benzo[a]anthraquinone ring system common to the angucycline antibiotics.

9. Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

10. Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

9. Direct C-H α-Arylation of Enones with ArI(O₂CR)₂ Reagents.