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Iridoids, 24 Biomimetic Synthesis of the Monoterpene Alkaloids Xylostosidine and Loxylostosidine A and of Similar Unnatural Compounds by Transformations of the Monoterpene Glycoside Secologanin
Author(s) -
Tietze Lutz F.,
Bärtels Christoph,
Fennen Jens
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890295
Subject(s) - monoterpene , chemistry , stereoselectivity , organic chemistry , glycoside , iridoid , yield (engineering) , condensation , stereochemistry , catalysis , materials science , metallurgy , physics , thermodynamics
Condensation of secologanim ( 1 ) with cysteamine ( 5a ) affords diastereoselectively 71% of xylostosidine ( 2 ), which was transformed into loxylostosidine A ( 3 ) by treatment with m ‐chloroperbenzoic acid in 70% yield. Similarly, reaction of the functionalized amines 5b , c , 6a–c , and 7 with 1 yields the unnatural monoterpene alkaloids 8–13 . The condensation of 1 with 5a was followed by time‐resolved NMR spectroscopy to reveal the stereoselectivity in this transformation.