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Title: Synthesis of Polycyclic Spirocarbocycles via Acid-Promoted Ring-Contraction/Dearomative Ring-Closure Cascade of Oxapropellanes
Authors: Ogawa, Naoki
Yamaoka, Yousuke
Takikawa, Hiroshi  kyouindb  KAKEN_id  orcid (unconfirmed)
Takasu, Kiyosei  kyouindb  KAKEN_id  orcid (unconfirmed)
Author's alias: 小川, 直希
山岡, 庸介
瀧川, 紘
高須, 清誠
Issue Date: Sep-2019
Publisher: American Chemical Society (ACS)
Journal title: Organic letters
Volume: 21
Issue: 18
Start page: 7563
End page: 7567
Abstract: We report herein the development of an acid-promoted rearrangement of oxa[4.3.2]propellanes to afford polyaromatic-fused spiro[4.5]carbocycles. DFT calculations suggest that the reaction pathway involves generation of a cyclobutyl cation, ring contraction to the cyclopropylcarbinyl cation, and dearomative ring closure by an internal 2-naphthol moiety. The resulting spirocarbocycles are synthetically valuable, as they could be transformed into two different polycyclic aromatic hydrocarbons via skeletal rearrangement. Syntheses of optically pure spirocarbocycles via a central-to-axial-to-central chirality transfer are also described.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in 'Organic letters', copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
The full-text file will be made open to the public on 9 September 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1021/acs.orglett.9b02835
PubMed ID: 31497972
Appears in Collections:Journal Articles

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