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Synthesis of the rifamycin chromophore

✍ Scribed by T.Ross Kelly; Mohammad Behforouz; Antonio Echavarren; Jacob Vaya

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 306 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)81917-6

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✦ Synopsis

A regiospecific, Diels-Alder based synthesis of the naphthofuranone chromophore (1) of the rifamycins is described. The family of macrolides known as the rifamycins (e.g. L),l has attracted considerable synthetic interest recently. Most effort has focused on addressing the stereochemical problems embodied in the ansa bridge. 2 Construction of the naphthofuranone chromophore ring system itself (z), which is unique to the rifamycins, has received relatively scant attention: Kishi et al. have described a ca. 16-step synthesis of 2,3 -which was further elaborated during

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