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Literature DB >> 16834366

Macrolactonization via hydrocarbon oxidation.

Kenneth J Fraunhoffer¹, Narayanasamy Prabagaran, Lauren E Sirois, M Christina White.

Abstract

A novel Pd/sulfoxide-catalyzed macrolactonization reaction of linear omega-alkenoic acids is reported that proceeds via serial ligand-catalyzed allylic C-H oxidation. The scope of this macrolactonization appears to be very broad. Aryl, alkyl, and (Z)-alpha,beta-unsaturated acids are all competent nucleophiles for this reaction, with the latter undergoing macrolactonization with no olefin isomerization. High functional group compatibility is observed that includes biologically and medicinally relevant functionality such as ortho-substituted salicylate esters, bis(indoyl)maleimides, and peptides. Evidence is provided to support the hypothesis that macrolactonization proceeds via inner-sphere functionalization from a templated pi-allylPd carboxylate intermediate.

Entities: Chemical

Year: 2006 PMID： 16834366 PMCID： PMC2720785 DOI： 10.1021/ja063096r

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

13 in total

Review 1. Chemistry and biology of salicylihalamide a and related compounds.

Authors: Larry Yet
Journal: Chem Rev Date: 2003-11 Impact factor: 60.622

2. Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

Authors: Kosuke Namba; Yoshito Kishi
Journal: J Am Chem Soc Date: 2005-11-09 Impact factor: 15.419

3. Synthesis of functionalized salicylate esters and amides by photochemical acylation.

Authors: Omid Soltani; Jef K De Brabander
Journal: Angew Chem Int Ed Engl Date: 2005-03-04 Impact factor: 15.336

4. Synthesis of the macrocyclic core of laulimalide.

Authors: I Paterson; C De Savi; M Tudge
Journal: Org Lett Date: 2001-01-25 Impact factor: 6.005

Review 5. Macrolactonizations in the total synthesis of natural products.

Authors: A Parenty; X Moreau; J-M Campagne
Journal: Chem Rev Date: 2006-03 Impact factor: 60.622

6. Design, synthesis, and biological evaluation of HSP90 inhibitors based on conformational analysis of radicicol and its analogues.

Authors: Emilie Moulin; Vincent Zoete; Sofia Barluenga; Martin Karplus; Nicolas Winssinger
Journal: J Am Chem Soc Date: 2005-05-18 Impact factor: 15.419

7. Serial ligand catalysis: a highly selective allylic C-H oxidation.

Authors: Mark S Chen; Narayanasamy Prabagaran; Nathan A Labenz; M Christina White
Journal: J Am Chem Soc Date: 2005-05-18 Impact factor: 15.419

8. (S)-13-[(dimethylamino)methyl]-10,11,14,15-tetrahydro-4,9:16, 21-dimetheno-1H, 13H-dibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecene-1,3(2H)-d ione (LY333531) and related analogues: isozyme selective inhibitors of protein kinase C beta.

Authors: M R Jirousek; J R Gillig; C M Gonzalez; W F Heath; J H McDonald; D A Neel; C J Rito; U Singh; L E Stramm; A Melikian-Badalian; M Baevsky; L M Ballas; S E Hall; L L Winneroski; M M Faul
Journal: J Med Chem Date: 1996-07-05 Impact factor: 7.446

Review 9. Chemistry and biology of cyclic depsipeptides of medicinal and biological interest.

Authors: Francisco Sarabia; Samy Chammaa; Antonio Sánchez Ruiz; Laura Martín Ortiz; F Jorge López Herrera
Journal: Curr Med Chem Date: 2004-05 Impact factor: 4.530

10. A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation.

Authors: Mark S Chen; M Christina White
Journal: J Am Chem Soc Date: 2004-02-11 Impact factor: 15.419

32 in total

Macrolactonization via hydrocarbon oxidation.

Review 1. Chemistry and biology of salicylihalamide a and related compounds.

2. Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

3. Synthesis of functionalized salicylate esters and amides by photochemical acylation.

4. Synthesis of the macrocyclic core of laulimalide.

Review 5. Macrolactonizations in the total synthesis of natural products.

6. Design, synthesis, and biological evaluation of HSP90 inhibitors based on conformational analysis of radicicol and its analogues.

7. Serial ligand catalysis: a highly selective allylic C-H oxidation.

8. (S)-13-[(dimethylamino)methyl]-10,11,14,15-tetrahydro-4,9:16, 21-dimetheno-1H, 13H-dibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecene-1,3(2H)-d ione (LY333531) and related analogues: isozyme selective inhibitors of protein kinase C beta.

Review 9. Chemistry and biology of cyclic depsipeptides of medicinal and biological interest.

10. A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation.

1. Polyol synthesis through hydrocarbon oxidation: de novo synthesis of L-galactose.

2. syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.

3. Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

4. A chiral Lewis acid strategy for enantioselective allylic C-H oxidation.

5. Enantioselective synthesis of (-)-jiadifenin, a potent neurotrophic modulator.

6. Diversification of a β-Lactam Pharmacophore via Allylic C-H Amination: Accelerating Effect of Lewis Acid Co-Catalyst.

7. Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.

8. Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

9. Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

10. Aerobic Linear Allylic C-H Amination: Overcoming Benzoquinone Inhibition.