A convergent synthesis of the renin inhibitor CGP60536B

Sandham, David A.; Taylor, Roger; Carey, John; Fässler, Alexander

doi:10.1016/s0040-4039(00)01760-3

Cited by 51 publications

(42 citation statements)

References 8 publications

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“…The diastereoselective α‐alkylation of amide 18 , which was prepared from commercially available hex‐5‐ynoic acid ( 17 ), afforded the tertiary stereogenic center at C14 of the cladiellins 18. The superiority of pseudoephenamine as an auxiliary in asymmetric alkylation reactions involving isopropyl iodide as the electrophile allowed 19 to be prepared on a multigram scale 19. Successive hydrolysis and amide coupling reactions yielded a Weinreb amide, which was subsequently allowed to react with an acetylenyl Grignard reagent to give ketone 21 .…”

Section: Methodsmentioning

confidence: 99%

Collective Synthesis of Cladiellins Based on the Gold‐Catalyzed Cascade Reaction of 1,7‐Diynes

et al. 2014

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The cladiellin family of natural products, which includes molecules with various biological activities, continues to invite new synthetic studies. A gold-catalyzed tandem reaction of 1,7-diynes to construct the 6-5-bicyclic ring systems that are present in a number of natural products was developed. This reaction was applied as the key step to realize the formal and total syntheses of nine members of the cladiellin family in an enantio-and diastereoselective manner. This modular and efficient approach could also be used for the construction of other cladiellins, as well as their analogues, for follow-up studies.

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Section: Methodsmentioning

confidence: 99%

Collective Synthesis of Cladiellins Based on the Gold‐Catalyzed Cascade Reaction of 1,7‐Diynes

et al. 2014

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“…In work on peptide isosteres, the 1,6-dioxa-4azaspiro [4.4]nonane 45 was prepared (Scheme 11). 23 The substrate 43 can be prepared from (+)-pseudoephedrine isovaleramide. Treatment of 43 with NBS in DME-H 2 O provides the amide acetal 44 with a single configuration at the spirocenter and as a 6:1 mixture of trans/cis ring substituents.…”

Section: 6-dioxa-4-azaspiro[44]nonanementioning

confidence: 99%

Spirocyclic Orthoesters, Orthothioesters and Orthoaminals in the Synthesis and Structural Modification of Natural Products

Undheim

2016

Synthesis

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Spirocyclic scaffolds are embedded in several families of natural products. In the spirocyclic structure, the two rings constituting the spirane are linked through a common carbon atom. This review covers families of compounds that have three heteroatoms directly attached to the spirocarbon. Common heteroatoms are nitrogen, oxygen and sulfur, constituting spirocyclic orthoesters, ortholactones, orthothioesters and orthoaminals, or combinations thereof. Embedded spirocyclic scaffolds introduce steric restrictions and thereby influence bioactivity. In polymer chemistry, synthetic ortholactones may serve as monomers. Synthesis of anomeric spironucleosides will afford molecules where the basic unit is in a fixed conformation around the N-glycosidic bond. Synthesis of glycosidic and 2-deoxyglycosidic ortholactones in disaccharides and regioselective reductive cleavage of cyclic orthoesters result in stereoselective β-(1→4)-glycosidic bond formation. Pyranose and furanose free-radical chemistry via spirocyclic orthoesters can be applied in the generation of carbacyclic sugars and nucleosides. 1 Introduction 2 Heteraspiro[3.m]alkanes 3 Heteraspiro[4.m]alkanes 4 Heteraspiro[5.m]alkanes 5 Conclusion Key words tri(α-hetera)spiranes, spiroannulations, stereoselective syntheses, spirocyclic nucleosides, spirocyclic glycosides, polymer monomers 2 Heteraspiro[3.m]alkanes 2.1 Heteraspiro[3.4]octanes 2.1.1 5,8-Dioxa-1-azaspiro[3.4]octane Cyclic ketene acetals react with phenyl isocyanate to afford the corresponding spiro compounds. Scheme 1 shows a synthesis of a spirane, 6-methyl-1-phenyl-5,8-dioxa-2-oxo-1-azaspiro[3.4]octane (2). 12 In general, the β-carbon atom in the double bond of ketene acetals has an anionic character and forms an equimolar adduct with isocyanates. The adduct formation is often exothermic and may be carried out neat or in a solvent. In the preparation of 2, control of SYNTHESIS0 0

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“…157,158 A number of synthetic approaches [159][160][161][162] to aliskiren have been patented [163][164][165][166][167] by Novartis and Speedel Pharma (Basel, Switzerland) or published in a number of original articles. [168][169][170][171][172][173] Synthetic strategies 174 are often based on visual imaging of a target structure. 175 For several aliskiren syntheses, a highly enantioselective hydrogenation of a selected substrate has been chosen to insert a chiral center.…”

Section: Rh-catalyzed Hydrogenation To Drug and Natural Product Synthmentioning

confidence: 99%

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

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Asymmetric homogeneous hydrogenation is perhaps one of the most researched areas in homogeneous catalysis; thus, it is now used in numerous innovative applications in stereoselective syntheses of many chiral pharmaceutical and natural products. Metal complexes, derived from transition metals, like Rh, Ru, Ir, and so on, and chiral ligands (usually mono‐ or diphosphine ligands), are widely used as catalysts in asymmetric alkene hydrogenation as a result of their efficiency in the preparation of enantiopure compounds with excellent atom economy. This chapter provides many interesting examples of homogeneous enantio‐ and diastereoselective hydrogenation of CC bonds, highlighting the utility of these methods as useful synthetic tools for the construction of stereogenic centers in stereoselective drug and natural product syntheses.

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A convergent synthesis of the renin inhibitor CGP60536B

Cited by 51 publications

References 8 publications

Collective Synthesis of Cladiellins Based on the Gold‐Catalyzed Cascade Reaction of 1,7‐Diynes

Collective Synthesis of Cladiellins Based on the Gold‐Catalyzed Cascade Reaction of 1,7‐Diynes

Spirocyclic Orthoesters, Orthothioesters and Orthoaminals in the Synthesis and Structural Modification of Natural Products

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

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