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Literature DB >> 18788741

Stereospecific total synthesis of somocystinamide A.

Abstract

The first total synthesis of somocystinamide A, a disulfide dimer with extremely labile enamide functional groups, was accomplished in a concise and stereospecific manner. Somocystinamide A is reported to possess exceptionally potent antiangiogenic and tumoricidal activities. The current work should enable further pharmacological investigation of this important natural product.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2008 PMID： 18788741 PMCID： PMC3227555 DOI： 10.1021/ol8016947

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

20 in total

1. Practical total syntheses of epiquinamide enantiomers.

Authors: Takashi L Suyama; William H Gerwick
Journal: Org Lett Date: 2006-09-28 Impact factor: 6.005

2. Combinatorial synthesis through disulfide exchange: discovery of potent psammaplin A type antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA).

Authors: K C Nicolaou; R Hughes; J A Pfefferkorn; S Barluenga; A J Roecker
Journal: Chemistry Date: 2001-10-01 Impact factor: 5.236

3. Brine shrimp: a convenient general bioassay for active plant constituents.

Authors: B N Meyer; N R Ferrigni; J E Putnam; L B Jacobsen; D E Nichols; J L McLaughlin
Journal: Planta Med Date: 1982-05 Impact factor: 3.352

4. Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula.

Authors: Zunxue Chang; Namthip Sitachitta; James V Rossi; Mary Ann Roberts; Patricia M Flatt; Junyong Jia; David H Sherman; William H Gerwick
Journal: J Nat Prod Date: 2004-08 Impact factor: 4.050

5. Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation.

Authors: Gerald Pattenden; Neil J Ashweek; Charles A G Baker-Glenn; James Kempson; Gary M Walker; James G K Yee
Journal: Org Biomol Chem Date: 2008-03-06 Impact factor: 3.876

6. Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors: Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal: Org Lett Date: 2003-10-02 Impact factor: 6.005

7. Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines.

Authors: Larry E Overman; Takaaki Sato
Journal: Org Lett Date: 2007-11-15 Impact factor: 6.005

8. Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950.

Authors: Robert S Coleman; Pei-Hua Liu
Journal: Org Lett Date: 2004-02-19 Impact factor: 6.005

4. Transcriptional analysis of the jamaicamide gene cluster from the marine cyanobacterium Lyngbya majuscula and identification of possible regulatory proteins.

Authors: Adam C Jones; Lena Gerwick; David Gonzalez; Pieter C Dorrestein; William H Gerwick
Journal: BMC Microbiol Date: 2009-12-01 Impact factor: 3.605

4 in total

Stereospecific total synthesis of somocystinamide A.

1. Practical total syntheses of epiquinamide enantiomers.

2. Combinatorial synthesis through disulfide exchange: discovery of potent psammaplin A type antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA).

3. Brine shrimp: a convenient general bioassay for active plant constituents.

4. Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula.

5. Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation.

6. Copper-catalyzed coupling of amides and carbamates with vinyl halides.

7. Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines.

8. Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950.

9. Rhodium-catalyzed methylenation of aldehydes.

10. CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

Review 1. Biologically active secondary metabolites from marine cyanobacteria.

2. Metabolites from an endophytic fungus sphaceloma sp. LN-15 isolated from the leaves of Melia azedarach.

Review 3. Biosurfactants Produced by Marine Microorganisms with Therapeutic Applications.

4. Transcriptional analysis of the jamaicamide gene cluster from the marine cyanobacterium Lyngbya majuscula and identification of possible regulatory proteins.