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Synthesis of Spinosyn Analogues for Modern Crop Protection
Author(s) -
Tietze Lutz F.,
Schützenmeister Nina,
Grube Alexander,
Scheffer Timo,
Baag Mohammad Merajuddin,
Granitzka Markus,
Stalke Dietmar
Publication year - 2012
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.201200600
Subject(s) - chemistry , moiety , cyclopentene , stereochemistry , rhamnose , cyclopentanone , heck reaction , organic chemistry , catalysis , palladium , polysaccharide
Abstract New spinosyn analogues 3 with an arene group as ring A and containing a L ‐rhamnose moiety have been prepared. The key step in the synthesis of 3 is a Pd‐catalyzed twofold Heck reaction of glycosylated bromoarene 4 , containing an iodovinyl side chain and a tri‐ O ‐methyl‐ L ‐rhamnose moiety with the cyclopentene‐annulated macrolactone 5 . Compounds 3 may be of interest as new insecticides.