Open AccessPreparation and Synthetic Applications of 8-Oxabicyclo[3.2.1]oct-6-en-3-one Derivatives
Author(s) -
Sylvain Favre,
Sandrine GerberLemaire,
Pierre Vogel
Publication year - 2008
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2008.221
Subject(s) - synthon , desymmetrization , stereoselectivity , chemistry , total synthesis , combinatorial chemistry , stereochemistry , resolution (logic) , enantioselective synthesis , organic chemistry , computer science , programming language , catalysis
The development of efficient routes to multi-gram quantities of chiral synthons is a key issue in the total synthesis of natural products and analogues. The conformationally defined and rigid 8-oxabicyclo[3.2.1]oct-6-en-3-one template is an appealing starting material for the development of non-iterative approaches to polyoxygenated fragments that are found in a large variety of biologically relevant natural compounds. Desymmetrization and resolution procedures, stereoselective functionalizations and double-chain elongations represent attractive strategies for such synthetic challenges.