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6‐Substituted Indanoyl Isoleucine Conjugates Mimic the Biological Activity of Coronatine
Author(s) -
Schüler Göde,
Görls Helmar,
Boland Wilhelm
Publication year - 2001
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 - 10.1002/1099-0690(200105)2001:9<1663::aid-ejoc1663>3.0.co;2-i
Subject(s) - chemistry , coronatine , acylation , conjugate , isoleucine , tendril , carboxylic acid , stereochemistry , intramolecular force , organic chemistry , biochemistry , amino acid , arabidopsis , leucine , botany , mathematical analysis , mathematics , mutant , gene , biology , catalysis
The 6‐substituted indanoyl isoleucine conjugates of type 12 are potent elicitors of plant secondary metabolism and tendril coiling. The 6‐substituted indanoyl carboxylic acid is available in four steps from 1,2,3,4‐tetrahydronaphthalene ( 6 ). Key steps of the synthesis involve double acylation of 6 followed by oxidative cleavage and intramolecular Friedel−Crafts acylation of the resulting dicarboxylic acid 10 . The conjugate with isoleucine ( 12 ) triggers volatile biosynthesis in the Lima bean at 10 µ M and coiling of the touch‐sensitive tendrils of Bryonia dioica at 20 µ M .