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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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
20.01.2017
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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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. |
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Bibliography: | KAKEN ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.6b03541 |