Vicinal Tricarbonyl Compounds: Versatile Building Blocks for Natural Product Synthesis

Dedicated to Prof. Dieter Enders on the occasion of his 70^th birthday

Abstract

Due to their high density of functional groups, vicinal tri­carbonyl compounds are versatile building blocks for the synthesis of complex target molecules. Methods for their preparation and their use in stereoselective C–C bond formations, as well as for the synthesis of heteroaromatics, are summarised for the period 2006–2016. Several examples for their applications in natural product synthesis (awajanomycin, cladoniamide, wailupemycin) are presented.

1 Introduction

2 Preparation of Vicinal Tricarbonyl Compounds

3 Use in Stereoselective C–C Bond Formations

4 Use for the Synthesis of Heteroaromatics

5 Examples from Natural Product Synthesis

6 Conclusion

Key words

vicinal tricarbonyl compounds - stereoselective synthesis - natural products - total synthesis - regioselectivity

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