Recent Advances in the Synthesis of Angucyclines

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 of cyclobutenones 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.

• 1 Introduction

• 2 Diels-Alder Reactions

• 2.1 Formation of B Ring: DC+A Strategy

• 2.2 Formation of C Ring: D+BA Strategy

• 2.3 Formation of D Ring from a Dienophile Bearing the CBA Moiety

• 3 Friedel-Crafts Reactions

• 4 Nucleophilic Additions

• 4.1 Anionic Annulations with Phthalides

• 4.2 Other Anionic Annulations

• 5 Free Radical Annulations

• 6 Rearrangements of Cyclobutenones

• 7 Cobalt-Mediated [2+2+2] Cycloadditions

• 8 Summary

angucyclines - asymmetric synthesis - synthetic ­methods - quinones - total synthesis

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