AN IMPROVED SYNTHESIS OF 6,8-DIMETHOXY-3-METHYLISOCOUMARIN, A FUNGAL METABOLITE PRECURSOR
AN IMPROVED SYNTHESIS OF 6,8-DIMETHOXY-3-METHYLISOCOUMARIN, A FUNGAL METABOLITE PRECURSOR
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DOI：
10.1021/jo00278a043
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发表时间：
1989-08-18
影响因子：
3.6
通讯作者：
SCHULTZ, TP
中科院分区：
文献类型：
--
作者：
KENDALL, JK;FISHER, TH;SCHULTZ, TP
南松甲虫和山松甲虫分别是对美国南部和北美西部松林最具破坏性的两种昆虫。角鼻虫属的真菌，通常被称为蓝斑真菌，与这些松甲虫都是共生的，而小角鼻虫是每种情况下存在的主要真菌物种。众所周知，蓝染真菌感染会破坏松树的水分蒸腾过程，从而导致枯萎。3,4,6虽然这一致病过程的机制尚不清楚，但一些异香豆素的代谢物已被牵连。4 . heocoumarins la和lb经海明威（hemingway）和麦格劳（McGraw）鉴定为主要代谢物。最近，Ayer5报道了从C. minor培养物中分离出的更长的代谢物清单，包括la-c， 2a-c和ceratenolone（一种铁螯合天然产物）。6,8 -二羟基-3-甲基异香豆素（la）也在其他角鼻虫物种中被发现，2包括荷兰榆树病的病原体C. ulmi 9。a. R= Me；R'= R'= H b. R'= R'= H c. R= R'= m；这项工作的目的是开发一种有效的合成异香豆素Id，然后可以用作合成异香豆素la-c和2a-c的前体。本研究的长期目标是确定这些异香豆素真菌代谢物在宿主树死亡中所起的作用。
The southern pine beetle1 and the mountain pine beetle2 are the two most destructive insects to the pine forests of the southern United States and western North America, respectively. Fungi of the genus Ceratocystis, often called blue-stain fungi, are symbiotically associated with each of these pine beetles, and Ceratocystis minor is the principal fungus species present in each case. 3" 5 Blue-stain fungal infections are known to disrupt the pine water transpira-tion process, which leads to wilting. 3, 4, 6 Although the mechanism of this pathogenic process is unknown, several isocoumarin metabolites of C. minor have been implicated. 4 Isocoumarins la and lb were isolated and identified as major metabolites of C. minor by Hemingway7 and McGraw. 8 Recently, Ayer5 reported a more lengthy list of metabolites isolated from C. minor cultures that included la-c, 2a-c, and ceratenolone, an iron-chelating natural product. 6, 8-Dihydroxy-3-methylisocoumarin (la) has also been found in other Ceratocystis species, 2 in-cluding C. ulmi, 9 the causative agent of Dutch elm disease.1 a. R= Me; R'= R"= H b. R= CHjOH i R'= R"= H c. R= R'= Me; R"= H d. R= R'= R"= MeThe objective of this work was to develop an efficient synthesis of isocoumarin Id that could then be used as a precursor for syntheses of isocoumarins la-c and 2a-c. The long-range goal of this research is to determine the role that these isocoumarin fungal metabolites play in the death of the host tree.