Skeletal Rearrangements of Polycyclic α‑Ketols
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 rearra...
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Published in | Organic letters Vol. 19; no. 2; pp. 301 - 303 |
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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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AbstractList | 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. 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. 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. |
Author | Kawamura, Moe Azuma, Shuhei Kuramochi, Kouji Tsubaki, Kazunori Tokitoh, Norihiro Kubo, Konomi Kamo, Shogo Sasamori, Takahiro |
AuthorAffiliation | Kyoto University Tokyo University of Science Graduate School of Life and Environmental Sciences Kyoto Prefectural University Department of Applied Biological Science, Faculty of Science and Technology Institute for Chemical Research |
AuthorAffiliation_xml | – name: Kyoto Prefectural University – name: Graduate School of Life and Environmental Sciences – name: Tokyo University of Science – name: Kyoto University – name: Institute for Chemical Research – name: Department of Applied Biological Science, Faculty of Science and Technology |
Author_xml | – sequence: 1 givenname: Moe surname: Kawamura fullname: Kawamura, Moe – sequence: 2 givenname: Shogo surname: Kamo fullname: Kamo, Shogo – sequence: 3 givenname: Shuhei surname: Azuma fullname: Azuma, Shuhei – sequence: 4 givenname: Konomi surname: Kubo fullname: Kubo, Konomi – sequence: 5 givenname: Takahiro surname: Sasamori fullname: Sasamori, Takahiro – sequence: 6 givenname: Norihiro surname: Tokitoh fullname: Tokitoh, Norihiro – sequence: 7 givenname: Kouji orcidid: 0000-0003-0571-9703 surname: Kuramochi fullname: Kuramochi, Kouji email: kuramoch@rs.tus.ac.jp – sequence: 8 givenname: Kazunori surname: Tsubaki fullname: Tsubaki, Kazunori |
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Snippet | It has been proposed that prekinamycin and kinobscurinone may biogenetically isomerize to isoprekinamycin and prefluostatin, respectively, through the... |
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Title | Skeletal Rearrangements of Polycyclic α‑Ketols |
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