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261 Newest Publications in organic letters

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One-Pot Protocol to Functionalized Benzopyrrolizidine Catalyzed Successively by Rh2(OAc)4 and Cu(OTf)2: A Transition Metal–Lewis Acid Catalysis Relay

12-12-2014 | Hua-Dong Xu; Zhi-Hong Jia; Ke Xu; Hao Zhou; Mei-Hua Shen, Organic Letters, 2014

4-N-Allylarylpropylamino-1-sulfonyl triazoles are converted to structurally unique benzopyrrolizidinyl sulfonamides in a one-pot operation. Intramolecular capture of rhodium carbene with arylamino nitrogen gives rise to the formation of an ammonium ylide immediate. A [2,3]- or [1,2]-rearrangement ...

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First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)

12-12-2014 | Barbara Pokorny; Paul Kosma, Organic Letters, 2014

Resistance of bacterial pathogens toward antibiotics has revived interest in lipopolysaccharide (LPS) motifs as potential therapeutic targets. The LPS of several pathogenic Acinetobacter strains comprises a 4,5-branched Kdo trisaccharide containing an uncommon (2→5)-linkage. In this contribution ...

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Substrate-Controlled Michael Additions of Chiral Ketones to Enones

25-11-2014 | Mireia Fàbregas; Alejandro Gómez-Palomino; Miquel Pellicena; Daniel F. Reina; Pedro Romea; Fèlix Urpí; Mercè Font-Bardia, Organic Letters, 2014

Substrate-controlled Michael additions of the titanium(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. ...

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Brønsted Acid Mediated Alkenylation and Copper-Catalyzed Aerobic Oxidative Ring Expansion/Intramolecular Electrophilic Substitution of Indoles with Propargyl Alcohols: A Novel One-Pot Approach to Cyclopenta[c]quinolines

17-11-2014 | G. Gangadhararao; Anasuyamma Uruvakilli; K. C. Kumara Swamy, Organic Letters, 2014

Copper-catalyzed oxidative ring-expansion/intramolecular electrophilic substitution of 3-dienylindoles leading to cyclopenta[c]quinolines and 3-indenylindoles under aerobic conditions is described. The precursors, 3-dienylindoles, are formed via Friedel–Crafts alkenylation followed by ...

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A Cascade of Acid-Promoted C–O Bond Cleavage and Redox Reactions: From Oxa-Bridged Benzazepines to Benzazepinones

14-11-2014 | Yuewei Zhang; Fengzhi Yang; Lianyou Zheng; Qun Dang; Xu Bai, Organic Letters, 2014

Organic Letters DOI: 10.1021/ol502971e

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Resorcylic Acid Lactone Biosynthesis Relies on a Stereotolerant Macrocyclizing Thioesterase

05-11-2014 | Graham W. Heberlig; Monica Wirz; Meng Wang; Christopher N. Boddy, Organic Letters, 2014

Zearalenone and radicicol are highly related resorcylic acid lactones with the rare property of having opposite stereochemical configurations of the secondary alcohol involved in lactone formation. The ability of the thioesterases from the zearalenone and radicicol biosynthetic pathways to ...

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Unusual Pyrimidine Participation: Efficient Stereoselective Synthesis of Potent Dual Orexin Receptor Antagonist MK-6096

03-11-2014 | John Y. L. Chung; Yong-Li Zhong; Kevin M. Maloney; Robert A. Reamer; Jeffrey C. Moore; Hallena Strotman; Alexei Kali ..., Organic Letters, 2014

An asymmetric synthesis of dual orexin receptor antagonist MK-6096 (1) is described. Key steps for the trans-2,5-disubstituted piperidinyl ether fragment include a biocatalytic transamination, a trans-selective Mukaiyama aldol, and a regioselective pyridyl SNAr process. The pyrimidyl benzoic acid ...

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Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

30-10-2014 | Chicco Manzuna Sapu; Tamás Görbe; Richard Lihammar; Jan-E. Bäckvall; Jan Deska, Organic Letters, 2014

A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Brønsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. ...

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Brevisulcatic Acids, Marine Ladder-Frame Polyethers from the Red Tide Dinoflagellate Karenia brevisulcata in New Zealand

30-10-2014 | Rina Suzuki; Raku Irie; Yanit Harntaweesup; Kazuo Tachibana; Patrick T. Holland; D. Tim Harwood; Feng Shi; Veronica ..., Organic Letters, 2014

The isolation and structural determination of new marine ladder-frame polyethers, brevisulcatic acids-1 (1) and -4 (2) are reported. Brevisulcatic acids were isolated from the dinoflagellate Karenia brevisulcata, which was identified as the causative species of a major red tide event in New ...

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TMIO-PyrImid Hybrids are Profluorescent, Site-Directed Spin Labels for Nucleic Acids

28-10-2014 | Benjamin A. Chalmers; Subham Saha; Tri Nguyen; John McMurtrie; Snorri Th. Sigurdsson; Steven E. Bottle; Kye-Simeon M ..., Organic Letters, 2014

We report the synthesis of a new class of molecules which are hybrids of long-lived tetramethylisoindolinoxyl (TMIO) radicals and the pyrido[1,2-a]benzimidazole (PyrImid) scaffold. These compounds represent a new lead for noncovalently binding nucleic acid probes, as they interact with nucleic ...

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