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Seven-Membered Rings


Smith, Jason and Ryan, JH, Seven-Membered Rings, Progress in Heterocyclic Chemistry, Elsevier, G.W. Gribble and J.A. Joule (ed), Amsterdam, pp. 432-458. ISBN 978-0-08-046975-1 (2009) [Research Book Chapter]

DOI: doi:10.1016/S0959-6380(09)70021-2


This chapter discusses both fused and non-fused heterocycles, focusing on N, O, and S as the heteroatoms of the seven-membered ring components. The chemistry and biological activities of seven-membered heterocyclic compounds continues to command significant attention. The chapter highlights on research describing the construction of these systems. A continuing trend has been the synthesis of seven-membered derivatives of biologically active molecules, such as carbohydrates and nucleic acids. Many synthetic methods for the synthesis of seven-membered rings are simply the extensions of methodology for the lower homologues; therefore, particular attention has been given to synthetic methods that specifically target the titled systems. Reviews focussing on the featured systems during 2007 have covered the medicinal chemistry of the 1,4-diazepines and the synthesis of macrocyclic shellfish toxins containing spiroimine moieties. Azepine based azasugars are formed from chiral cyclohexyl derivatives, formed from D-(-)-quinic acid, by the oxidative cleavage of a diol or the ozonolysis of an alkene to yield a dialdehyde followed by reductive amination forming the heterocyclic system The tandem-Staudinger-aza Wittig mediated ring expansion of a 6-azido pyranoside is used to yield isofagomine derivatives.

Item Details

Item Type:Research Book Chapter
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Smith, Jason (Associate Professor Jason Smith)
ID Code:62404
Year Published:2009
Deposited By:Chemistry
Deposited On:2010-03-11
Last Modified:2015-03-24

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