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Literature DB >> 20078122

Valence tautomerism in titanium enolates: catalytic radical haloalkylation and application in the total synthesis of neodysidenin.

Stéphane Beaumont¹, Elizabeth A Ilardi, Lucas R Monroe, Armen Zakarian.

Abstract

A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed. The chloroalkylation method served as the centerpiece in the enantioselective total synthesis of trichloroleucine-derived marine natural product neodysidenin.

Entities: Chemical Disease Gene

Mesh：

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Year: 2010 PMID： 20078122 PMCID： PMC2819066 DOI： 10.1021/ja910154f

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

14 in total

1. Characterization of the initial enzymatic steps of barbamide biosynthesis.

Authors: Patricia M Flatt; Susan J O'Connell; Kerry L McPhail; Gloria Zeller; Christine L Willis; David H Sherman; William H Gerwick
Journal: J Nat Prod Date: 2006-06 Impact factor: 4.050

2. Unconventional biradical character of titanium enolates.

Authors: I de P R Moreira; J M Bofill; J M Anglada; J G Solsona; J Nebot; P Romea; F Urpí
Journal: J Am Chem Soc Date: 2008-02-21 Impact factor: 15.419

3. ADDITION OF CARBON TETRACHLORIDE AND CHLOROFORM TO OLEFINS.

Authors: M S Kharasch; E V Jensen; W H Urry
Journal: Science Date: 1945-08-03 Impact factor: 47.728

4. Structure of (-)-neodysidenin from Dysidea herbacea. Implications for biosynthesis of 5,5,5-trichloroleucine peptides.

Authors: J B MacMillan; E K Trousdale; T F Molinski
Journal: Org Lett Date: 2000-08-24 Impact factor: 6.005

Review 5. Vanadium haloperoxidases.

Authors: A Butler
Journal: Curr Opin Chem Biol Date: 1998-04 Impact factor: 8.822

6. The role of the achiral template in enantioselective transformations. Radical conjugate additions to alpha-methacrylates followed by hydrogen atom transfer.

Authors: Mukund P Sibi; Justin B Sausker
Journal: J Am Chem Soc Date: 2002-02-13 Impact factor: 15.419

7. New lipopeptides from the Caribbean cyanobacterium Lyngbya majuscula.

Authors: J I Jiménez; P J Scheuer
Journal: J Nat Prod Date: 2001-02 Impact factor: 4.050

8. Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Authors: Christian Nilewski; Roger W Geisser; Erick M Carreira
Journal: Nature Date: 2009-01-29 Impact factor: 49.962

9. Sintokamides A to E, chlorinated peptides from the sponge Dysidea sp. that inhibit transactivation of the N-terminus of the androgen receptor in prostate cancer cells.

Authors: Marianne D Sadar; David E Williams; Nasrin R Mawji; Brian O Patrick; Thamrin Wikanta; Ekowati Chasanah; Hari Eko Irianto; Rob Van Soest; Raymond J Andersen
Journal: Org Lett Date: 2008-10-04 Impact factor: 6.005

10. Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

Authors: Grant M Shibuya; Jacob S Kanady; Christopher D Vanderwal
Journal: J Am Chem Soc Date: 2008-08-22 Impact factor: 15.419

7 in total

4. A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates.

Authors: Aaron T Herrmann; Lindsay L Smith; Armen Zakarian
Journal: J Am Chem Soc Date: 2012-04-12 Impact factor: 15.419

Valence tautomerism in titanium enolates: catalytic radical haloalkylation and application in the total synthesis of neodysidenin.

1. Characterization of the initial enzymatic steps of barbamide biosynthesis.

2. Unconventional biradical character of titanium enolates.

3. ADDITION OF CARBON TETRACHLORIDE AND CHLOROFORM TO OLEFINS.

4. Structure of (-)-neodysidenin from Dysidea herbacea. Implications for biosynthesis of 5,5,5-trichloroleucine peptides.

Review 5. Vanadium haloperoxidases.

6. The role of the achiral template in enantioselective transformations. Radical conjugate additions to alpha-methacrylates followed by hydrogen atom transfer.

7. New lipopeptides from the Caribbean cyanobacterium Lyngbya majuscula.

8. Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

9. Sintokamides A to E, chlorinated peptides from the sponge Dysidea sp. that inhibit transactivation of the N-terminus of the androgen receptor in prostate cancer cells.

10. Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

1. Concise total synthesis of sintokamides A, B, and E by a unified, protecting-group-free strategy.

2. Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

3. Dual Ti-Ru catalysis in the direct radical haloalkylation of N-acyl oxazolidinones.

4. A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates.

5. Titanium Radical Redox Catalysis: Recent Innovations in Catalysts, Reactions, and Modes of Activation.

Review 6. Thiazole and oxazole alkaloids: isolation and synthesis.

7. Stereoselective α-Tertiary Alkylation of N-(Arylacetyl)oxazolidinones.