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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Summary: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.
Bibliography:KAKEN
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03541