Sesquiterpenes

This chapter first presents a discussion on biosynthesis, and then focuses cycloisomerization reactions in organic synthesis, especially on the biocorrelated diene and enyne counterparts, and finally discusses the cycloisomerization power to some selected total syntheses of sesquiterpenoids. Followi...

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Bibliographic Details
Published inFrom Biosynthesis to Total Synthesis pp. 236 - 278
Main Authors Zografos, Alexandros L, Anagnostaki, Elissavet E
Format Book Chapter
LanguageEnglish
Published Hoboken, NJ John Wiley & Sons, Inc 22.04.2016
Subjects
biosynthesis
cycloisomerization
farnesyl diphosphate
geranyl diphosphate
isopentenyl diphosphate
organic synthesis
sesquiterpenoids
total synthesis
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Summary:This chapter first presents a discussion on biosynthesis, and then focuses cycloisomerization reactions in organic synthesis, especially on the biocorrelated diene and enyne counterparts, and finally discusses the cycloisomerization power to some selected total syntheses of sesquiterpenoids. Following the biosynthetic mechanism, initial ionization of geranyl diphosphate (GDP) to the cation followed by the subsequent addition of the isopentenyl diphosphate (IDP) unit forms the farnesyl diphosphate (FDP) cation in a reaction that is catalyzed by farnesyl pyrophosphate synthase (FPPS) prenyltransferase. Transition metal‐catalyzed cycloisomerizations have been the subject of particular attention as atom‐efficient methods for the construction of carbo‐ and heterocyclic molecules. Several studies concerning their metal‐catalyzed cyclization mechanisms have been undertaken in α,ω‐bifunctional substrates such as dienes, enynes, and diynes. The chapter concentrates on catalyzed reactions, which are triggering different cyclization modes, only for the construction of sesquiterpene core structures.
ISBN:1118751736
9781118751732
DOI:10.1002/9781118754085.ch7