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Synthesis of Carbocyclic Homo‐ N ‐Nucleosides from Iridoids
Author(s) -
Franzyk Henrik,
Rasmussen Jon Holbech,
Mazzei Raffaele Antonio,
Jensen Søren Rosendal
Publication year - 1998
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/(sici)1099-0690(199812)1998:12<2931::aid-ejoc2931>3.0.co;2-c
Subject(s) - chemistry , catalpol , trifluoromethanesulfonate , regioselectivity , mitsunobu reaction , moiety , yield (engineering) , iridoid , stereochemistry , salt (chemistry) , organic chemistry , glycoside , catalysis , materials science , metallurgy
Two iridoid glucosides, antirrhinoside ( 1 ) and catalpol ( 2 ), were converted into selectively protected polysubstituted cyclopentylmethanols, which were subsequently used to prepare carbocyclic homo‐ N ‐nucleosides ( 5 , 6 and 14 ). A purine moiety was introduced either by the Mitsunobu reaction or by substitution of a primary triflate with the tetrabutylammonium salt of 6‐iodopurine. The latter method was superior with regard to both ease of purification and yield. The N‐9 vs. N‐7 regioselectivity of the salts of different 6‐substituted purine derivatives was briefly investigated.