环合方法可实现复杂倍半萜伯克利酮 A 的全合成。
Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A.
机构信息
Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
出版信息
J Am Chem Soc. 2016 Nov 16;138(45):14868-14871. doi: 10.1021/jacs.6b10397. Epub 2016 Nov 8.
Synthetic pathways to complex meroterpenes derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl pyrophosphate have not been reported despite heavy biosynthetic and medicinal interest. Herein we report the first total synthesis of berkeleyone A, a potential gateway compound to a plethora of fungal-derived meroterpenes, in 13 steps. In addition, we have further developed a novel annulation reaction for the synthesis of hydroxylated 1,3-cyclohexadiones in a single step.
尽管人们对 3,5-二甲基奥尔酸（DMOA）和法呢基焦磷酸酯衍生的复杂倍半萜类化合物有着浓厚的生物合成和药用兴趣，但目前还没有报道其合成途径。在此，我们报告了伯克利酮 A 的首次全合成，伯克利酮 A 是一种潜在的多真菌来源倍半萜类化合物的前体化合物，共 13 步。此外，我们还进一步开发了一种新的环合反应，可在一步中合成羟基化的 1,3-环己二酮。
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