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Bridgehead Substitution via Putative Norborn-1-en-3-ones: Application in the Synthesis of Complex Molecules.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2015 May 04; Vol. 21 (19), pp. 7021-5. Date of Electronic Publication: 2015 Mar 24. - Publication Year :
- 2015
-
Abstract
- The base-mediated formation of a bridgehead double bond in a bicyclo[2.2.1]heptane system (anit-Bredt molecules) is described. The synthesis of exocyclic norbornyl enones by Wittig reaction of α-diketones is reported. These enones and their Michael adducts are used as substrates for the generation of transient bridgehead enones and their trapping with MeOH and H2 O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products.<br /> (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 21
- Issue :
- 19
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 25810279
- Full Text :
- https://doi.org/10.1002/chem.201500131