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Synthesis 2007(21): 3261-3285  
DOI: 10.1055/s-2007-990831
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approaches to Naturally Occurring Ten-Membered-Ring Lactones

Helena M. C. Ferraz*a,†, Fernanda I. Bombonatoa, Luiz S. Longo Jr*b
a Instituto de Química, Universidade de São Paulo, CP 26077, 05513-970 São Paulo, SP, Brazil
b Universidade Federal de São Paulo, Campus Diadema, 09972-270 Diadema, SP, Brazil
e-Mail: luiz.longo@unifesp.br;
Further Information

Publication History

Received 27 June 2007
Publication Date:
16 October 2007 (online)

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Abstract

The strategies for the synthesis of naturally occurring ten-membered-ring lactones, which are the most abundant of the medium-ring lactones, are discussed. According to their structures and/or biosynthesis, the molecules are classified in monocyclic polyketides, monocyclic oxylipins, aliphatic bicyclic and aromatic bicyclic lactones. In each subsection, the lactones are presented in chronological order of their isolation. Representative complex systems bearing multiple functionalities in addition to the lactone moiety, as well as a selection of recent synthetic approaches to non-natural medium-ring lactones, are briefly presented.

1 Introduction

2 Monocyclic Ten-Membered-Ring Lactones

2.1 Polyketides

2.2 Oxylipins

3 Bicyclic Ten-Membered-Ring Lactones

3.1 Aliphatic

3.2 Aromatic

4 Complex Ten-Membered-Ring Lactones

5 Non-natural Lactones: Selected Synthetic Approaches

6 Conclusion

Key words

natural products - medium-sized-ring systems - ten-membered-ring lactones - monocyclic lactones - bicyclic lactones