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Literature DB >> 18596842

Concise, Biomimetic Total Synthesis of d,l-Marcfortine C.

Thomas J Greshock¹, Alan W Grubbs, Robert M Williams.

Abstract

A biomimetic total synthesis of the fungal metabolite marcfortine C utilizing an intramolecular Diels-Alder reaction is described. In addition, a key stereoselective oxaziridine-mediated oxidation/pinacol rearrangement of indole 24 was used to complete the total synthesis.

Entities: Chemical

Year: 2007 PMID： 18596842 PMCID： PMC2346435 DOI： 10.1016/j.tet.2007.03.016

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

23 in total

1. Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide.

Authors: Andrew G Myers; Seth B Herzon
Journal: J Am Chem Soc Date: 2003-10-08 Impact factor: 15.419

2. The isolation of brevianamide A from Penicillium ochraceum.

Authors: J E Robbers; J W Straus
Journal: Lloydia Date: 1975 Jul-Aug

3. A concise total synthesis of the notoamides C and D.

Authors: Alan W Grubbs; Gerald D Artman; Sachiko Tsukamoto; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.

Authors: Hikaru Kato; Takushi Yoshida; Takanori Tokue; Yuka Nojiri; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams; Sachiko Tsukamoto
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Disposition of Mycophenolic Acid, Brevianamide A, Asperphenamate, and Ergosterol in Solid Cultures of Penicillium brevicompactum.

Authors: B A Bird; I M Campbell
Journal: Appl Environ Microbiol Date: 1982-02 Impact factor: 4.792

6. Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides.

Authors: R M Banks; S E Blanchflower; J R Everett; B R Manger; C Reading
Journal: J Antibiot (Tokyo) Date: 1997-10 Impact factor: 2.649

Review 7. Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.

Authors: Robert Michael Williams
Journal: Chem Pharm Bull (Tokyo) Date: 2002-06 Impact factor: 1.645

8. Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G.

Authors: J M Liesch; C F Wichmann
Journal: J Antibiot (Tokyo) Date: 1990-11 Impact factor: 2.649

9. Production, isolation, and preliminary toxicity studies of brevianamide A from cultures of Penicillium viridicatum.

Authors: B J Wilson; D T Yang; T M Harris
Journal: Appl Microbiol Date: 1973-10

10. Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A.

Authors: Barry B Snider; Hongbo Zeng
Journal: J Org Chem Date: 2003-01-24 Impact factor: 4.354

19 in total

1. Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

Authors: Konrad Sommer; Robert M Williams
Journal: Tetrahedron Date: 2008-07-21 Impact factor: 2.457

Review 2. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors: Kenneth A Miller; Robert M Williams
Journal: Chem Soc Rev Date: 2009-09-16 Impact factor: 54.564

Concise, Biomimetic Total Synthesis of d,l-Marcfortine C.

1. Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide.

2. The isolation of brevianamide A from Penicillium ochraceum.

3. A concise total synthesis of the notoamides C and D.

4. Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.

5. Disposition of Mycophenolic Acid, Brevianamide A, Asperphenamate, and Ergosterol in Solid Cultures of Penicillium brevicompactum.

6. Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides.

Review 7. Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.

8. Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G.

9. Production, isolation, and preliminary toxicity studies of brevianamide A from cultures of Penicillium viridicatum.

10. Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A.

1. Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

Review 2. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Review 3. Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

4. Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

5. Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.

6. Oxidative reactions of tetrahydrobenzimidazole derivatives with N-sulfonyloxaziridines.

7. Calmodulin inhibitory activity of the malbrancheamides and various analogs.

8. Biomimetic total synthesis of malbrancheamide and malbrancheamide B.

9. Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B.

10. Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.