Synthesis 2013; 45(7): 845-873
DOI: 10.1055/s-0032-1318152
review
© Georg Thieme Verlag Stuttgart · New York

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

Thanh Vinh Nguyen
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   eMail: enders@rwth.aachen.de
,
Jan Marc Hartmann
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   eMail: enders@rwth.aachen.de
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   eMail: enders@rwth.aachen.de
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 02. Januar 2013

Accepted: 04. Januar 2013

Publikationsdatum:
04. März 2013 (online)


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