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Synthesis of Carbohydrate‐Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1‐Vinylcycloalkenes
Author(s) -
Dolhem Franck,
Lièvre Catherine,
Demailly Gilles
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300102
Subject(s) - chemistry , yield (engineering) , metathesis , enyne , ring closing metathesis , enyne metathesis , grubbs' catalyst , monosaccharide , carbohydrate chemistry , salt metathesis reaction , organic chemistry , catalysis , ring (chemistry) , stereochemistry , polymerization , materials science , metallurgy , polymer
In this paper, a new route toward polyhydroxylated 1‐vinylcycloalkenes is presented. 1,6‐ and 1,7‐enynes were synthesized in four steps from glyco‐ynitols, which are readily available from monosaccharides. These compounds were then cyclized by ring‐closing enyne metathesis to afford the title compounds. For example, we converted (2 R ,3 S ,4 R )‐1‐ O ‐tritylhept‐6‐yne‐1,2,3,4‐tetrol ( 1 ) to the corresponding 1,7‐enyne 13 in 53% yield. The ring‐closing metathesis of 1,7‐enyne 13 with Grubbs catalyst, under Mori’s conditions, produced the corresponding polyhydroxylated 1‐vinylcyclohexene 19 in 72% yield. The conversion of several glyco‐ynitols into polyhydroxylated 1‐vinylcycloalkenes was carried out with satisfying yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)