Healy Alan R, Vinale Francesco, Lorito Matteo, Westwood Nicholas J
School of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM , North Haugh, St. Andrews, Fife KY169ST, U.K.
Org Lett. 2015 Feb 6;17(3):692-5. doi: 10.1021/ol503717r. Epub 2015 Jan 28.
The bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.
生物活性天然产物哈茨酸首次仅通过六个步骤（最长线性序列）制备而成，总产率为22%。确定将酰胺键形成和Lacey-Dieckmann反应合并到一锅反应中的条件被证明很重要。哈茨酸的三种立体异构体也已制备出来，为比较它们的生物活性提供了材料。虽然所有异构体都促进了根系生长，但出人意料的是，对映体系列中与哈茨酸相反的异构体具有更高的抗真菌活性。
