SYNTHESIS OF NEW, UNNATURAL MACROCYCLIC TRICHOTHECENES - 3-ISOVERRUCARIN-A ((1''-O)(3-]4)ABEO-VERRUCARIN-A), VERRUCINOL, AND VERRUCENE .46.
SYNTHESIS OF NEW, UNNATURAL MACROCYCLIC TRICHOTHECENES - 3-ISOVERRUCARIN-A ((1''-O)(3-]4)ABEO-VERRUCARIN-A), VERRUCINOL, AND VERRUCENE .46.
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DOI：
10.1002/hlca.19880710808
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发表时间：
1988-01-01
影响因子：
1.8
通讯作者：
TAMM, C
中科院分区：
文献类型：
--
作者：
JEKER, N;TAMM, C
A new unnatural macrocyclic trichothecene, an analogue of verrucarine A (1), which was named 3-Isoverrucarin A ((1''''-O)(3.fwdarw.4)abeo-verrucarin A; 3) was synthesized starting from anguidine (5). The two key reactions were the removal of the 4.beta.-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.
