Abstract

The different strategies recently reported to construct the tetracyclic skeleton of angucyclines are presented: Diels-Alder and Friedel-Crafts reactions, nucleophilic additions, free radical annulations, rearrangements ofcyclobutenones and cobalt-mediated [2+2+2] cycloadditions. Among the asymmetric approaches, the most efficient corresponds to Diels-Alder reactions including the use of chiral catalysts, enantiopure vinyl cyclohexenes as dienes, synthesized from quinic acid or (S,S)-[(p-tolylsulfinyl)methyl]-p-quinol, and chiral dienophiles such as (S,S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones.

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