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Literature DB >> 20563264

New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products.

Abstract

We report the application of diphenyloxazinone glycinate chiral templates to asymmetric syntheses of cylindrospermospin, 7-epi-cylindrospermopsin, 7-deoxycylindrospermopsin, and spirotryprostatins A and B. Synthetic studies toward quinine, nakadomarin A, and palau'amine using these templates are also described.

Entities: Chemical Disease Species

Year: 2009 PMID： 20563264 PMCID： PMC2886987

Source DB: PubMed Journal: ACS Symp Ser Am Chem Soc ISSN： 0097-6156

20 in total

1. A Rapid Total Synthesis of Spirotryprostatin B: Proof of Its Relative and Absolute Stereochemistry F.v.N. gratefully acknowledges the Alexander-von-Humboldt-Stiftung for a Feodor-Lynen fellowship that was kindly backed by Dr. R. Breslow as second host. This research was supported by the National Institutes of Health (Grant number HL 25848). We thank Dr. H. Osada (RIKEN) for providing us with spectra of the natural product. Furthermore we are grateful to Dr. D. Lichtblau from the Nakanishi laboratory for help with the CD spectra. We acknowledge the collaborative efforts of Ms. Maria Manzoni in these studies.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-06-16 Impact factor: 15.336

2. Stereoselective total synthesis of the cyanobacterial hepatotoxin 7-epicylindrospermopsin: revision of the stereochemistry of cylindrospermopsin.

Authors: G R Heintzelman; W K Fang; S P Keen; G A Wallace; S M Weinreb
Journal: J Am Chem Soc Date: 2001-09-12 Impact factor: 15.419

3. Catalytic asymmetric total syntheses of quinine and quinidine.

Authors: Izzat T Raheem; Steven N Goodman; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2004-01-28 Impact factor: 15.419

4. Preparation and synthetic applications of 2-halotryptophan methyl esters: synthesis of spirotryprostatin B.

Authors: Fumiko Y Miyake; Kenichi Yakushijin; David A Horne
Journal: Angew Chem Int Ed Engl Date: 2004-10-11 Impact factor: 15.336

5. Total Synthesis of (-)-Spirotryprostatin B and Three Stereoisomers We thank NIH NIGMS (GM-30859) for financial support, Prof. A. J. Shaka and N. D. Taylor for DPFGSE experiments, Prof. H. Osada for providing spectral data for natural 1, and Prof. R. M. Williams and P. R. Sebahar for providing spectral data and a sample of synthetic ent-21. We are also grateful to Prof. R. M. Williams and Prof. S. J. Danishefsky for open exchange of information prior to publication. NMR and mass spectra were determined at UC Irvine with instruments purchased with the assistance of the NSF and NIH shared instrumentation programs.

Authors: Larry E. Overman; Mark D. Rosen
Journal: Angew Chem Int Ed Engl Date: 2000-12-15 Impact factor: 15.336

Review 3. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors: Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal: Nat Prod Rep Date: 2011-05-09 Impact factor: 13.423

3 in total

New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products.

2. Stereoselective total synthesis of the cyanobacterial hepatotoxin 7-epicylindrospermopsin: revision of the stereochemistry of cylindrospermopsin.

3. Catalytic asymmetric total syntheses of quinine and quinidine.

4. Preparation and synthetic applications of 2-halotryptophan methyl esters: synthesis of spirotryprostatin B.

6. The pursuit of palau'amine.

7. Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus.

8. The first stereoselective total synthesis of quinine.

9. Concise, asymmetric total synthesis of spirotryprostatin A.

10. A concise asymmetric synthesis of the ADE fragment of nakadomarin A.

1. Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition.

Review 2. Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Review 3. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.