The total synthesis of the fungal metabolite diversonol
The total synthesis of the fungal metabolite diversonol
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DOI：
10.1002/anie.200502913
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发表时间：
2006-01-01
影响因子：
16.6
通讯作者：
Bräse, S
中科院分区：
文献类型：
--
作者：
Nising, CF;Ohnemüller, UK;Bräse, S
霉菌毒素是真菌产生的次生代谢产物，是具有有趣生物活性的物质来源。[1]癸二酸 (1) 代表由麦角菌以及各种其他真菌产生的一类物质。 [2]癸二酸是具有 2, 2’-联芳基单元的对称或不对称四氢呫吨酮二聚体。由于最近已分离出具有类似结构的其他霉菌毒素，其中许多显示出有前景的生物活性，因此有效合成此类物质将非常有用。 [3]在我们对癸二酸的全合成进行研究的过程中，我们还对次生代谢物地弗森醇 (2) 的合成感兴趣，它是由 Turner 从 Penicillium diversum 中分离出来的，其结构基序也可以在上述一些物质中找到。迄今为止，天然存在的地松醇的绝对构型尚不清楚。[4]由于地松醇的结构与癸二酸单体的结构非常相似，因此地松醇的全合成也将是迈向癸二酸全合成的一步。由于官能团的高密度——所有四个羟基都彼此靠近，因此预计地敌醇的合成具有挑战性。
Mycotoxins, which are secondary metabolites produced by fungi, are a source of substances with interesting biological activity.[1] The secalonic acids (1) represent a class of substances produced by Claviceps purpurea as well as various other fungi.[2] The secalonic acids are symmetrical or unsymmetrical tetrahydroxanthenone dimers possessing a 2, 2’-biaryl unit. Since other mycotoxins with a similar structure have been isolated recently, many of which show promising biological activity, an efficient synthetic access to this substance class would be very useful.[3] In the course of our studies towards the total synthesis of the secalonic acids, we were also interested in the synthesis of the secondary metabolite diversonol (2), which was isolated by Turner from Penicillium diversum and whose structural motif can also be found in some of the substances mentioned above. The absolute configuration of naturally occurring diversonol is not known to date.[4]As the structure of diversonol is very similar to that of the secalonic acid monomers, the total synthesis of diversonol would also be a step towards the total synthesis of the secalonic acids. The synthesis of diversonol was expected to be challenging owing to the high density of functional groups—all four hydroxy groups are located close to each