An unexpected re-arrangement of the antibiotic carbapenem core to new 1, 4-diazepin-5-one scaffolds. Issue 1 (19th December 2017)

• Record Type: Journal Article
• Authors: Peters, Byron K.; Razuwika, Rufaro; Samipillai, Marivel; Arvidsson, Per I.; Kruger, Hendrik G.; Govender, Thavendran; Naicker, Tricia
• Is Part Of: RSC advances. Volume 8:Issue 1(2018)
• Page Start: 190
• Page End: 193
• Publication Date: 2017-12-19
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra12688c
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Herein we report a peculiar organocatalyzed domino-reaction on the carbapenem core structure. Abstract : Herein we report a peculiar organocatalyzed domino-reaction on the carbapenem core structure. As previously reported, 30 mol% of proline yields diazabicyclo[4.2.1]nonane analogues, while we currently report the formation of novel 1, 4-diazepin-5-ones from the same starting material in the presence of 100 mol% proline. The inherent chirality of the starting material led to the stereochemical preference of the products with excellent diastereoselectivity (>99 : 1). The diazepinone products were confirmed using X-ray diffraction and 2D-NMR structure elucidation. A plausible mechanism of the re-arrangement, involving an unactivated retro -Dieckmann condensation, is also presented.