Skeletal Rearrangements of Polycyclic α-Ketols
Skeletal Rearrangements of Polycyclic α-Ketols
复制标题
DOI：
10.1021/acs.orglett.6b03541
复制
发表时间：
2017-01-20
期刊：
影响因子：
5.2
通讯作者：
Tsubaki, Kazunori
中科院分区：
文献类型：
--
作者：
Kawamura, Moe;Kamo, Shogo;Tsubaki, Kazunori
有人提出，前激霉素和激那霉素酮可以通过相应的桥头α-酮醇中间体分别生物异构化为异前激霉素和前氟他汀。在此转化中，6-5环系统通过α-酮醇重排转化为5-6环系统。在本报告中，报道了受这种假设的生物合成转化启发的多环α-酮醇的骨架重排。此外，。还报道了从二苯并[b]芴到苯并[g]色烯的意外重排。
It has been proposed that prekinamycin and kinobscurinone may biogenetically isomerize to isoprekinamycin and prefluostatin, respectively, through the corresponding bridgehead a-ketol intermediates. In this transformation, the 6-5 ring system is converted into a 5-6 ring system via an a-ketol rearrangement. In this report, the skeletal rearrangement of polycyclic a-ketols inspired by this hypothetical biosynthetic transformation is reported. In addition,. an unexpected rearrangement from dibenzo[b]fluorene to benzo[g]chromene is also reported.