Skeletal Rearrangements of Polycyclic α-Ketols
- Moe Kawamura ,
- Shogo Kamo ,
- Shuhei Azuma ,
- Konomi Kubo ,
- Takahiro Sasamori ,
- Norihiro Tokitoh ,
- Kouji Kuramochi
, and - Kazunori Tsubaki
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† Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Kyoto 606-8522, Japan
‡ Department of Applied Biological Science, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan
§ Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
*E-mail: [email protected]
Abstract
It has been proposed that prekinamycin and kinobscurinone may biogenetically isomerize to isoprekinamycin and prefluostatin, respectively, through the corresponding bridgehead α-ketol intermediates. In this transformation, the 6–5 ring system is converted into a 5–6 ring system via an α-ketol rearrangement. In this report, the skeletal rearrangement of polycyclic α-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.
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