Recent Synthetic Strategies to Access Seven-Membered Carbocycles in Natural Product Synthesis

Abstract

This methodology-oriented review covers the synthetic strategies to construct seven-membered carbocycles in naturally occurring compounds over the last ten years. It offers an insight into the common synthetic targets and approaches and provides useful information for further developments within this area of natural product synthesis as well as synthetic methodology in general.

1 Introduction

2 Cyclization Reactions

3 Cycloaddition Reactions

3.1 [5+2] Cycloaddition

3.2 [4+3] Cycloaddition

3.3 Diels–Alder Reactions

3.4 [2+2+2] Cycloaddition

4 Ring-Closing Metathesis

4.1 Ene–Ene Metathesis

4.2 Ene–Yne Metathesis

5 Ring-Expansion and Ring-Contraction Reactions

5.1 Ring-Expansion Reactions

5.2 Ring-Contraction Reactions

6 Fragmentation and Isomerization Reactions

7 Other Frequently Targeted Natural Products

8 Conclusion

Key words

seven-membered carbocycles - natural products - total synthesis - synthetic strategy - medium-sized carbocycles

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