Iridoids, 24. - Biomimetic Synthesis of the Monoterpene Alkaloids Xylostosidine and Loxylostosidine A and of Similar Unnatural Compounds by Transformations of the Monoterpene Glycoside Secologanin
Condensation of secologanin (1) with cysteamine (5a) affords diastereoselectively 71percent of xylostosidine (2), which was transformed into loxylostosidine A (3) by treatement with m-chloroperbenzoic acid in 70percent 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.
Tietze, Lutz F.,Baertels, Christoph,Fennen, Jens
p. 1241 - 1246
(2007/10/02)
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