Strigol 유사체의 합성

Strigol, a natural product isolated from root exudates of cotton, was found to be an extremely potent seed germination stimulant for the parasitic plant, witchweed. Witchweed seeds can remain dormant in the soil for several years until favorable conditions prevail including exposure to some type of chemical germination stimulant. Several strigol analogues, 3-methyl-4-(2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-ylidenemethoxy)-but-2-en-4-olide(21), 4-(2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-ylidenemethoxy)but-2-en-4-oilde(22), 3-methyl-4-(2-oxotetrahydrofuran-3-ylidenemethoxy)-but-2-en-4-olide(23), and 4-(2-oxotetrahydrofuran-3-ylidenemethoxy)-but-2-en-4-olide(24), were synthesized. Strigol은 목화의 뿌리에서 추출된 천연물로서 벼, 옥수수, 사탕수수 등에 기생하는 피류(striga species) 등의 씨앗을 발아시키는데 월등한 효능을 보인다 $(10^{-12} ∼ 10^{-11}M, 80% 발아)$. 그런데 이러한 잡초는 오랜기간(15∼20년) 동안 흙속에서 휴면하고 있기 때문에 이들의 방제가 매우 어렵다. 이들을 방제할 수 있는 제초제 개발을 위해서 여러가지 strigol 유사체들인 3-methyl-4-(2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-ylidenemethoxy)-but-2-en-4-olide(21), 4-(2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-ylidenemethoxy)but-2-en-4-oilde(22), 3-methyl-4-(2-oxotetrahydrofuran-3-ylidenemethoxy)-but-2-en-4-olide(23), 4-(2-oxotetrahydrofuran-3-ylidenemethoxy)-but-2-en-4-olide(24)등을 합성하였다.