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New PDF release: Asymmetric synthesis of natural products

By Ari M. P. Koskinen

ISBN-10: 1118347323

ISBN-13: 9781118347324

ISBN-10: 1119976685

ISBN-13: 9781119976684

ISBN-10: 1119976693

ISBN-13: 9781119976691

ISBN-10: 1280775718

ISBN-13: 9781280775710

Asymmetric Synthesis of average Products, second version introduces scholars to this swiftly transforming into box of natural chemistry. The preliminary chapters current the rules of uneven synthesis, together with the idea and functions of person uneven reactions. this is often via chapters on all of the significant person periods of ordinary items; their buildings, biosynthesis and interrelationships in addition to examples of uneven syntheses and the sensible worth of those compounds. traditional product sessions lined contain carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, polyketides, isoprenoids, shikamic acid derivatives and alkaloids.

For this moment variation the textual content has been completely up to date and accelerated, and contains new discussions and examples overlaying atom and redox economies, useful features and environmental expertise. Organocatalysis has emerged thoroughly within the final ten years, and has been absolutely built-in into this new edition.

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Like α-amino acids generated by the Strecker reaction, β-amino acid derivatives accessible via Mannich reactions are important building blocks for the construction of natural products [33]. The N-galactosyl-βamino acid esters 67 were obtained by the treatment of silyl ketene acetals 62 with the Schiff bases 5 in the presence of zinc chloride at −78 to −30 °C within 24 h. 21). OSiMe3 OPiv PivO R' OMe O PivO N OPiv 5 R H OPiv PivO + OH OPiv O PivO R' 66 ZnCl2 Et2O OPiv PivO O PivO H 25 R' R 68 COOMe R' HCl/H2O ClR' + H3N HCl/MeOH H R' 90 C H R' COOMe OPiv R 67 THF/-78 C ClR' + H3N H N R 69 COOH Diastereoselective Mannich-type reaction of ketene acetals with imine 5 for the synthesis of β-alanine derivatives.

6) [20]. ) 23 Methyl 4,6-O-benzylidene-D-glucopyranoside NaI, 2-butanone, reflux 1) Pd(OH)2/C, H2, EtOH 2) TsCl, Et3N, DMAP, CH2Cl2 R1 HO TBSO Raney-Ni W4, EtOH (95%) O 24 O CH3CH=CHCO2H, TFAA, toluene Me TBSO OMe 33 Me O O TBSO TBSO OMe 27 (92%) 25: R1 = I 26: R1 = H CuBr•Me2S, R2MgX, THF-Me2S(2:1) R2 O Me O Xc 28 O Me Xc Me O O TBSO TBSO OMe 27 R2=vinyl,–78 to –18 °C, 88%, 90% de Et, –78 to –18 °C, 85%, 90% de Ph, –78 to 0 °C, 85%, 90% de R3 R3Li, O THF, —78 °C Me O Xc 29 R3= Et, 92%, 92% de t-Bu, 95%, 96% de Ph, 92%, 94% de 4M KOH-MeOH (1:1), reflux, then 1M HCl R Me 28 or 29 * O OH Me HO + HO HO OMe 31 (>90%) 30 (>90%) R=Et, t-Bu, or Ph O R DIBAL-H, CH2Cl2, –78 to –18 °C Me * OH 32 (>90%) + 26 (>90%) Synthesis of methyl 2,3-di-O-(t-butyldimethylsilyl)-6-deoxy-α-d-glucopyranoside 26 and subsequent 1,4-additions of organocuprates and organolithiums to its 4-O-crotonyl ester 27.

HF, –30 °C (83%) OH OSiMe3 PivO OPiv O PivO HO Xc TiCl4, (CH2Cl)2. ) PivO F 75 D-Galactose 43 R1 yield de Me Pr Ph 74% 84% 83% >90% 80% 100% O N Xc R1 77 Synthesis of N-(β-d-galactopyranosyl)-4-pyridone 76 and 1,4-additions of Grignard reagents to its 4-pyridone moiety. 14 providing 2-alkyl-substituted 5,6-dehydropiperidin-4-ones 77 in high yields. The carbohydrate auxiliary mediates a diastereoselective attack of the Grignard reagent at the planar 4-silyloxypyridinium intermediate; this constitutes a selective monofunctionalization and efficient diastereofacial differentiation of the two double bonds of the 4-pyridone in 76.

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Asymmetric synthesis of natural products by Ari M. P. Koskinen

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