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Molecular complexity from aromatics: synthesis and photoreaction of endo-tricyclo[5.2.2.02,6]undecanes. Formal total syntheses of (±)-coriolin

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Title Molecular complexity from aromatics: synthesis and photoreaction of endo-tricyclo[5.2.2.02,6]undecanes. Formal total syntheses of (±)-coriolin
 
Creator SINGH, VISHWAKARMA
SAMANTA, BISWAJIT
KANE, VINAYAK V
 
Subject cycloaddition
diels-alder reaction
photochemistry
polyquinanes
 
Description Formal syntheses of coriolin 1, a triquinane metabolite isolated from Coriolus consors, are described. Oxidation of 6-methyl saligenin 2 in the presence of cyclopentadiene gave the tricyclic keto epoxide 4 which was elaborated to tricyclo[5.2.2.02,6]undecenones 5 and 18 containing the major structural and stereochemical features of coriolin, in latent form. Triplet sensitized 1,2-acyl shifts in 5 and 18 gave tetracyclic compounds 6 and 19 in a stereoselective manner. Reductive cleavage of cyclopropane rings in 6 and 19 with H2/Pd-C and TBTH-AIBN respectively, furnished the functionalised triquinanes 7 and 20b which are known precursors for coriolin.
 
Publisher Elsevier
 
Date 2009-02-21T11:25:58Z
2011-11-25T17:17:28Z
2011-12-26T13:06:08Z
2011-12-27T05:53:56Z
2009-02-21T11:25:58Z
2011-11-25T17:17:28Z
2011-12-26T13:06:08Z
2011-12-27T05:53:56Z
2000
 
Type Article
 
Identifier Tetrahedron 56(39), 7785-7795
0040-4020
http://dx.doi.org/10.1016/S0040-4020(00)00674-8
http://hdl.handle.net/10054/726
http://dspace.library.iitb.ac.in/xmlui/handle/10054/726
 
Language en