期刊
TETRAHEDRON
卷 66, 期 35, 页码 7198-7203出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.06.072
关键词
Germination stimulants; Strigolactones; GR24 synthesis; Atom efficient synthesis; Bioassays; Parasitic weeds
An efficient and high yielding preparation for the synthetic germination stimulant GR24 (5) and its A-ring dimethyl-substituted analogues 30-32 has been described. The first step involves a Stobbe condensation of benzaldehydes 9-11 with dimethyl succinate. Subsequent transposition of the ester and reduction of the double bond provides the building blocks 15-17 for an intramolecular Friedel-Crafts acylation. ABC-lactones 22-25 are prepared from gamma-keto esters 18-21 by saponification, subsequent reduction with sodium borohydride followed by acid-catalyzed lactonization. Coupling of the lactones with the D-ring is accomplished by formylation and subsequent treatment with bromobutenolide 8 to give GR24 and its dimethyl analogues. Bioassays with Striga hermonthica seeds reveal that the dimethyl analogues are slightly less active than GR24 itself. (C) 2010 Elsevier Ltd. All rights reserved.
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