useful synthons, few syntheses of natural products and bioactive compounds, using
these synthons, have been described.
In chapter “Synthesis of 5,6- and 6,6-Spirocyclic Compounds,” M. A. Brimble
and L. A. Stubbing describe a number of recently reported and useful methods to
synthesize 5,6- and 6,6-spirocyclic compounds, including their applications to the
synthesis of natural products and bioactive compounds containing spiroacetal scaffolds. One can find dehydrative spirocyclization of dihydroxyketones, metal-catalyzed addition/elimination of allylic alcohols, acid-catalyzed spirocyclization of
hemiacetals, spirocyclization of exo- and endocyclic enol ethers, transition-metalcatalyzed hydroalkoxylation of alkynes, electrophilic cyclization and oxa-Michael
cyclization, intramolecular hetero-Michael addition, ring-opening of epoxides and
cyclopropanes, cycloadditions, furan oxidation, intramolecular hydrogen abstraction, reductive cyclizations, ring-closing metathesis, and rearrangements.
In chapter “Synthesis of Seven-Membered-Ring Ethers and Lactones,” O. Piva
describes the access to saturated oxygenated 7-membered cyclic ethers, by ring
expansion of oxygenated structures, by formation of C–O and C–C bonds using
different methods. For 7-membered cyclic lactones, oxidative processes, halolactonization, lactonization of ω-hydroxyacids, tandem Suzuki coupling and
lactonization, and ring enlargement are reported.
For the synthesis of 8- to 10-membered ring ethers, in chapter “Synthesis of
Eight- to Ten-Membered-Ring Ethers,” J. M. Contelles and E. Soriano focus on the
formation of carbon–carbon double bonds by metathesis, as well as on the formation of carbon–carbon single bonds. The authors also report on the cyclization to
form C–O bonds, ring expansion, ring-opening, and rearrangement.
Chapter “Synthesis of 12- to 16-Membered-Ring Lactones” is dedicated to the
synthesis of 12- to 16-membered ring lactones. In this chapter, M. Kalesse and
M. Cordes present an overview of the macrocyclization of seco-acids as well as new
effective procedures to access 12- to 16-membered ring lactones such as ringclosing metatheses of alkynes and olefins. The authors also report the use of ketene
sources and benzodioxinones to produce macrocyclic lactones. Nitrile oxide-olefin
cycloaddition, intramolecular C–H oxidative macrolactonization, and Yamaguchi
and Mukaiyama macrocyclization as well as macrolactonization via thioester or
using phosphorus reagents are described.
I would like to express my sincere gratitude to all the authors of these chapters
for their efforts and outstanding contributions. I would also like to thank B. Maes
for giving me the opportunity to edit these two volumes, to Elizabeth Hawkins and
Tanja Jaeger from Springer for coordinating the project, and to Fairin Miriam John
Bennet for the editing process, for her help and patience.
Finally, I hope that this book will be a good source of inspiration for those
planning the synthesis of saturated oxygenated heterocycles, for solving specific
synthetic problems, or for elaborating on new synthetic tools.
Paris, France
Janine Cossy
vi
Preface
these synthons, have been described.
In chapter “Synthesis of 5,6- and 6,6-Spirocyclic Compounds,” M. A. Brimble
and L. A. Stubbing describe a number of recently reported and useful methods to
synthesize 5,6- and 6,6-spirocyclic compounds, including their applications to the
synthesis of natural products and bioactive compounds containing spiroacetal scaffolds. One can find dehydrative spirocyclization of dihydroxyketones, metal-catalyzed addition/elimination of allylic alcohols, acid-catalyzed spirocyclization of
hemiacetals, spirocyclization of exo- and endocyclic enol ethers, transition-metalcatalyzed hydroalkoxylation of alkynes, electrophilic cyclization and oxa-Michael
cyclization, intramolecular hetero-Michael addition, ring-opening of epoxides and
cyclopropanes, cycloadditions, furan oxidation, intramolecular hydrogen abstraction, reductive cyclizations, ring-closing metathesis, and rearrangements.
In chapter “Synthesis of Seven-Membered-Ring Ethers and Lactones,” O. Piva
describes the access to saturated oxygenated 7-membered cyclic ethers, by ring
expansion of oxygenated structures, by formation of C–O and C–C bonds using
different methods. For 7-membered cyclic lactones, oxidative processes, halolactonization, lactonization of ω-hydroxyacids, tandem Suzuki coupling and
lactonization, and ring enlargement are reported.
For the synthesis of 8- to 10-membered ring ethers, in chapter “Synthesis of
Eight- to Ten-Membered-Ring Ethers,” J. M. Contelles and E. Soriano focus on the
formation of carbon–carbon double bonds by metathesis, as well as on the formation of carbon–carbon single bonds. The authors also report on the cyclization to
form C–O bonds, ring expansion, ring-opening, and rearrangement.
Chapter “Synthesis of 12- to 16-Membered-Ring Lactones” is dedicated to the
synthesis of 12- to 16-membered ring lactones. In this chapter, M. Kalesse and
M. Cordes present an overview of the macrocyclization of seco-acids as well as new
effective procedures to access 12- to 16-membered ring lactones such as ringclosing metatheses of alkynes and olefins. The authors also report the use of ketene
sources and benzodioxinones to produce macrocyclic lactones. Nitrile oxide-olefin
cycloaddition, intramolecular C–H oxidative macrolactonization, and Yamaguchi
and Mukaiyama macrocyclization as well as macrolactonization via thioester or
using phosphorus reagents are described.
I would like to express my sincere gratitude to all the authors of these chapters
for their efforts and outstanding contributions. I would also like to thank B. Maes
for giving me the opportunity to edit these two volumes, to Elizabeth Hawkins and
Tanja Jaeger from Springer for coordinating the project, and to Fairin Miriam John
Bennet for the editing process, for her help and patience.
Finally, I hope that this book will be a good source of inspiration for those
planning the synthesis of saturated oxygenated heterocycles, for solving specific
synthetic problems, or for elaborating on new synthetic tools.
Paris, France
Janine Cossy
vi
Preface