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Literature DB >> 22571279

Studies toward the synthesis of the epoxykinamycin FL-120B': discovery of a decarbonylative photocyclization.

Abstract

Photo-Friedel-Crafts acylation of a naphthoquinone was attempted in an effort to access a diazobenzofluorenone en route to the epoxykinamycin natural product FL-120B'. Photoirradiation of the naphthoquinone substrate which resulted in the unexpected formation of a tetracyclic naphthofuran via a decarbonylative photocyclization process is described.

Entities: Chemical

Mesh：

Substances：

Year: 2012 PMID： 22571279 PMCID： PMC3433630 DOI： 10.1021/ol3010563

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

13 in total

1. Two novel cytotoxic benzofuran derivatives from Brazilian propolis.

Authors: A H Banskota; Y Tezuka; K Midorikawa; K Matsushige; S Kadota
Journal: J Nat Prod Date: 2000-09 Impact factor: 4.050

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. Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation.

Authors: Aleksandra Baranczak; Gary A Sulikowski
Journal: Org Lett Date: 2012-02-06 Impact factor: 6.005

4. Structures and biological properties of Kinamycin A, B, C, and D.

Authors: S Omura; A Nakagawa; H Yamada; T Hata; A Furusaki
Journal: Chem Pharm Bull (Tokyo) Date: 1973-05 Impact factor: 1.645

5. A new antibiotic, kinamycin.

Authors: S Itŏ; T Matsuya; S Omura; M Otani; A Nakagawa
Journal: J Antibiot (Tokyo) Date: 1970-06 Impact factor: 2.649

Review 6. The diazofluorene antitumor antibiotics: structural elucidation, biosynthetic, synthetic, and chemical biological studies.

Authors: Seth B Herzon; Christina M Woo
Journal: Nat Prod Rep Date: 2011-10-28 Impact factor: 13.423

7. A catalytic homo-Nazarov cyclization protocol for the synthesis of heteroaromatic ring-fused cyclohexanones.

Authors: Lien H Phun; Dadasaheb V Patil; Marchello A Cavitt; Stefan France
Journal: Org Lett Date: 2011-03-18 Impact factor: 6.005

8. Photoinduced cyclization of 3-acyl-2-halo-1-[(ω-phenylethynyl)alkyl]indoles to azaheterocyclo[1,2,3-lm]-fused benzo[c]carbazoles.

Authors: Shenci Lu; Ren Wang; Yi Yang; Yang Li; Zongjun Shi; Wei Zhang; Zhifeng Tu
Journal: J Org Chem Date: 2011-06-15 Impact factor: 4.354

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

Authors: Xiaoguang Lei; John A Porco
Journal: J Am Chem Soc Date: 2006-11-22 Impact factor: 15.419

10. FL-120A-D', new products related to kinamycin from Streptomyces chattanoogensis subsp. taitungensis subsp. nov. II. Isolation and structure determination.

Authors: J J Young; S N Ho; W M Ju; L R Chang
Journal: J Antibiot (Tokyo) Date: 1994-06 Impact factor: 2.649

7 in total

Studies toward the synthesis of the epoxykinamycin FL-120B': discovery of a decarbonylative photocyclization.

1. Two novel cytotoxic benzofuran derivatives from Brazilian propolis.

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

3. Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation.

4. Structures and biological properties of Kinamycin A, B, C, and D.

5. A new antibiotic, kinamycin.

Review 6. The diazofluorene antitumor antibiotics: structural elucidation, biosynthetic, synthetic, and chemical biological studies.

7. A catalytic homo-Nazarov cyclization protocol for the synthesis of heteroaromatic ring-fused cyclohexanones.

8. Photoinduced cyclization of 3-acyl-2-halo-1-[(ω-phenylethynyl)alkyl]indoles to azaheterocyclo[1,2,3-lm]-fused benzo[c]carbazoles.

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

10. FL-120A-D', new products related to kinamycin from Streptomyces chattanoogensis subsp. taitungensis subsp. nov. II. Isolation and structure determination.

1. Multigram Synthesis of 1-O-Acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine.

2. Stereocontrolled Synthesis of the Fully Glycosylated Monomeric Unit of Lomaiviticin A.

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

4. Tandem dienone photorearrangement-cycloaddition for the rapid generation of molecular complexity.

5. Structure Revision of the Lomaiviticins.

6. Crystal structure of 7,8,9,10-tetra-hydro-benzo[b]naphtho-[2,1-d]furan.

7. Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A.