By Iwao Ojima, Edison S. Zuniga (auth.), Bimal K. Banik (eds.)
I. Ojima • E. S. Zuniga • J. D. Seitz: Advances within the Use of Enantiopure β-Lactams for the Synthesis of Biologically energetic Compounds of Medicinal Interests.- I. Fernández • Miguel A. Sierra: β -Lactams from Fischer Carbene Complexes: Scope, barriers, and response Mechanism.- Bablee Mandal • Basudeb Basu: Synthesis of β-Lactams via Alkyne–Nitrone Cycloadditions.- T. T. Tidwell: guidance of Bis-β-Lactams through Ketene–Imine Cycloadditions.- Edward Turos: The Chemistry and Biology of N-Thiolated β-Lactams.- Indrani Banik • Bimal okay. Banik: Synthesis of β-Lactams and Their Chemical Manipulations through Microwave-Induced Reactions.
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Extra resources for β-Lactams: Unique Structures of Distinction for Novel Molecules
Enantiopure 3-hydroxy-4-Rf-b-lactams (Rf ¼ fluorine-containing substituent) were obtained through (1) ketene–imine [2+2] cycloaddition followed by enzymatic resolution of the resulting racemic 3-acetoxyl-4-Rf-b-lactams with the PS Amano lipase or (2) functional group transformations of enatiopure 1-PMP-3-TIPSO-4-(2-methylprop1-enyl)azetidin-2-one, (3R,4S)-216a or (3S,4R)-216a . 9% ee in high yields (Scheme 66) [12, 50, 122]. 4-Trifluoromethyl-b-lactams, (+)-226 and (À)-227, with >99% ee 42 I.
2eq), Et3N, CH3CN, 55 °C, 24 h iii) HF-py,CH3CN,16h AcO O OH O HO O O O N H OH O OAc O 258 Scheme 75 Synthesis of conformationally restricted paclitaxel congener via Heck reaction SBT-2054 bearing the double bond conjugated to the benzoyl moiety, in good yield after deprotection (Scheme 74) [143b]. This novel process is mediated by the Ru complex, but not catalytic, and proposed to involve Ru-allyl complexes as key intermediates [143b]. The biological activities of these macrocyclic taxoids, mimicking the tubulin-bound structure of paclitaxel, were examined for their tubulin polymerization and microtubule stabilization potencies as well as cytotoxicities against six human cancer cell lines.
Cl2Ru(=CHPh)(PCy3)2 CH2Cl2, r. , 71% ii. HF/Py, Py, MeCN 80% O OH O HN O O OH H OAc O HO OBz O SBT-2054 Scheme 74 Synthesis of conformationally restricted macrocyclic paclitaxel congeners via ring-closing metathesis Advances in the Use of Enantiopure b-Lactams for the Synthesis of. . 2eq), Et3N, CH3CN, 55 °C, 24 h iii) HF-py,CH3CN,16h AcO O OH O HO O O O N H OH O OAc O 258 Scheme 75 Synthesis of conformationally restricted paclitaxel congener via Heck reaction SBT-2054 bearing the double bond conjugated to the benzoyl moiety, in good yield after deprotection (Scheme 74) [143b].