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Literature DB >> 20515072

Efficient total synthesis of ammosamide B.

P V Narasimha Reddy¹, Biplab Banerjee, Mark Cushman.

Abstract

A total synthesis of ammosamide B, a metabolite of the marine-derived Streptomyces strain CNR-698, has been executed in nine steps and 6.9% overall yield. The key step involves the condensation of a 4,6-diBoc-protected 1,3,4,6-tetraaminobenzene derivative with dimethyl 2-ketoglutaconate, which effectively constructs the pyrrolidinone ring and the quinoline ring in a single step. This contributes a unique approach to the synthesis of pyrroloquinoline alkaloids that offers the advantages of brevity and relatively high overall yield.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2010 PMID： 20515072 PMCID： PMC2894265 DOI： 10.1021/ol101215x

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

7 in total

1. Lymphostin (LK6-A), a novel immunosuppressant from Streptomyces sp. KY11783: taxonomy of the producing organism, fermentation, isolation and biological activities.

Authors: H Nagata; K Ochiai; Y Aotani; K Ando; M Yoshida; I Takahashi; T Tamaoki
Journal: J Antibiot (Tokyo) Date: 1997-07 Impact factor: 2.649

2. Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport.

Authors: Christina N Carrigan; Richard D Bartlett; C Sean Esslinger; Kimberly A Cybulski; Pakamas Tongcharoensirikul; Richard J Bridges; Charles M Thompson
Journal: J Med Chem Date: 2002-05-23 Impact factor: 7.446

3. Synthesis of Pyrrolo[4,3,2-de]quinolines from 6,7-Dimethoxy-4-methylquinoline. Formal Total Syntheses of Damirones A and B, Batzelline C, Isobatzelline C, Discorhabdin C, and Makaluvamines A-D.

Authors: David Roberts; John A. Joule; M. Antonieta Bros; Mercedes Alvarez
Journal: J Org Chem Date: 1997-02-07 Impact factor: 4.354

4. Total synthesis of the ammosamides.

Authors: Chambers C Hughes; William Fenical
Journal: J Am Chem Soc Date: 2010-03-03 Impact factor: 15.419

Review 5. Pyrroloiminoquinone and related metabolites from marine sponges.

Authors: Edith M Antunes; Brent R Copp; Michael T Davies-Coleman; Toufiek Samaai
Journal: Nat Prod Rep Date: 2005-01-04 Impact factor: 13.423

6. Ammosamides A and B target myosin.

Authors: Chambers C Hughes; John B MacMillan; Susana P Gaudêncio; William Fenical; James J La Clair
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. The ammosamides: structures of cell cycle modulators from a marine-derived Streptomyces species.

Authors: Chambers C Hughes; John B MacMillan; Susana P Gaudêncio; Paul R Jensen; William Fenical
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7 in total

5 in total

1. Design, synthesis, and biological evaluation of potent quinoline and pyrroloquinoline ammosamide analogues as inhibitors of quinone reductase 2.

Authors: P V Narasimha Reddy; Katherine C Jensen; Andrew D Mesecar; Phillip E Fanwick; Mark Cushman
Journal: J Med Chem Date: 2011-12-29 Impact factor: 7.446

Efficient total synthesis of ammosamide B.

1. Lymphostin (LK6-A), a novel immunosuppressant from Streptomyces sp. KY11783: taxonomy of the producing organism, fermentation, isolation and biological activities.

2. Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport.

3. Synthesis of Pyrrolo[4,3,2-de]quinolines from 6,7-Dimethoxy-4-methylquinoline. Formal Total Syntheses of Damirones A and B, Batzelline C, Isobatzelline C, Discorhabdin C, and Makaluvamines A-D.

4. Total synthesis of the ammosamides.

Review 5. Pyrroloiminoquinone and related metabolites from marine sponges.

6. Ammosamides A and B target myosin.

7. The ammosamides: structures of cell cycle modulators from a marine-derived Streptomyces species.

1. Design, synthesis, and biological evaluation of potent quinoline and pyrroloquinoline ammosamide analogues as inhibitors of quinone reductase 2.

2. Ammosamide D, an oxidatively ring opened ammosamide analog from a marine-derived Streptomyces variabilis.

3. Precursor-Directed Generation of Amidine Containing Ammosamide Analogs: Ammosamides E-P.

Review 4. A look around the West Indies: The spices of life are secondary metabolites.

5. A biosynthetic pathway to aromatic amines that uses glycyl-tRNA as nitrogen donor.