Title of article
A pattern recognition approach to 14-epi-hydrophenanthrene core of the morphine alkaloids based on shikimic acid
Author/Authors
Tung N. Dinh، نويسنده , , Anqi Chen، نويسنده , , Christina L.L. Chai، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
6
From page
3363
To page
3368
Abstract
An expeditious and stereoselective construction of C-14-epimer of the tetracyclic hydrophenanthrene framework of the morphine alkaloids is described. The core structure is obtained in nine steps in 11% overall yield from shikimic acid via three key transformations: (i) coupling of shikimic acid with 2-iodoisovanillin at C-3 by double SN2 inversion to form the aryl ether 5; (ii) an intramolecular Heck reaction to construct the dihydrobenzofuran ring and (iii) a McMurry coupling to furnish the hydrophenanthrene core.
Keywords
Intramolecular McMurry coupling , Pattern recognition , Hydrophenanthrene , Shikimic acid , Intramolecular Heck coupling
Journal title
Tetrahedron
Serial Year
2011
Journal title
Tetrahedron
Record number
1103189
Link To Document