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 inOrganic letters Vol. 19; no. 2; pp. 301 - 303
Main Authors Kawamura, Moe, Kamo, Shogo, Azuma, Shuhei, Kubo, Konomi, Sasamori, Takahiro, Tokitoh, Norihiro, Kuramochi, Kouji, Tsubaki, Kazunori
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.01.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KINAMYCIN
GENE-CLUSTER
HETEROLOGOUS EXPRESSION
IDENTIFICATION
STREPTOMYCES-AURANTICOLOR
ANTICOCCIDIAL ANTIBIOTICS
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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.
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
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Keywords KINAMYCIN
GENE-CLUSTER
HETEROLOGOUS EXPRESSION
IDENTIFICATION
STREPTOMYCES-AURANTICOLOR
ANTICOCCIDIAL ANTIBIOTICS
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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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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Skeletal Rearrangements of Polycyclic α‑Ketols
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