Bridgehead substitution via putative norborn-1-en-3-ones: Application in the synthesis of complex molecules

Khan, Faiz Ahmed and Budanur, B M and Chava, S (2015) Bridgehead substitution via putative norborn-1-en-3-ones: Application in the synthesis of complex molecules. Chemistry - A European Journal, 21 (19). pp. 7021-7025. ISSN 0947-6539

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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 H2O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products.

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IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	anti-Bredt;bridgehead alcohols;enones;rearrangements;strained molecules
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	11 May 2015 04:15
Last Modified:	21 Sep 2017 06:21
URI:	http://raiithold.iith.ac.in/id/eprint/1501
Publisher URL:	https://doi.org/10.1002/chem.201500131
OA policy:	http://www.sherpa.ac.uk/romeo/issn/0947-6539/
Related URLs:	Google Scholar

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