A new unnatural macrocyclic trichothecene, an analogue of verrucarine A (1), which was named 3-Isoverrucarin A ((1″-O)(34)abeo-verrucarin A; 3) was synthesized starting from anguidine (5). The two key reactions were the removal of the 4β-acetoxy group of anguidine (5) by a Barton deoxygenation and the final macrolactonization. During the cyclization procedure, two unexpected new macrocyclic by-products, which were named verrucinol (19) and verrucene (20), were formed. They represent novel types of macrocyclic trichothecenes, the macrolidic moiety of verrucene (20) consisting only of the (Z,E)-muconic-acid residue. The formation of the analogous macrolide 26 of verrucene (20) was not possible, probably because the ring strain is too strong.

中文翻译：

---

新的合成，非天然大环单端孢：3- isoverrucarin A（（1“ - ö）（34）的abeo- -verrucarin A），verrucinol，和verrucene。第46次关于Verrucarins和roridins的交流^†

一种新的非天然大环单端孢，verrucarine A的（模拟1），将其命名为3- Isoverrucarin A（（1“ - ö）（34）的abeo- -verrucarin A; 3）合成从anguidine（起始5）。这两个关键反应是通过Barton脱氧和最终的大内酯化作用去除了胍基（5）的4β-乙酰氧基。在环化过程中，形成了两种出乎意料的新的大环副产物，分别称为Verrucinol（19）和Verrucene（20）。它们代表新类型的大环毛孢菌烯，即Verrucene的大分子部分（20）仅由（Z，E）-粘康酸残基组成。Verrucene（20）的类似大环内酯26的形成是不可能的，可能是因为环应变太强了。