Construction of Functionalized ortho-Naphthoquinone Methides via Site-Selective Ring Opening of 1-Siloxy-1,4-epoxy-1,4-dihydronaphthalenes

Aijima, Takaaki; Komagawa, Shinsuke; Akai, Shuji et al.

Advanced Synthesis and Catalysis, 2023, 365(22), 3981-3986

アクセス数:60件（2025-04-10 08:28 集計）

固定URL: https://hdl.handle.net/11094/93212

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タイトル
Construction of Functionalized ortho-Naphthoquinone Methides via Site-Selective Ring Opening of 1-Siloxy-1,4-epoxy-1,4-dihydronaphthalenes
著者
著者名
Aijima, Takaaki
著者名
Komagawa, Shinsuke
NRID
1000060192457 1000060192457
researchmap permalink
shuji_akai shuji_akai
Scopus Author ID
7006001526 7006001526
ORCID
0000-0001-9149-8745 0000-0001-9149-8745
著者名
Akai, Shuji
NRID
1000080552413 1000080552413
researchmap permalink
sawama sawama
Scopus Author ID
6505798196 6505798196
ORCID
0000-0002-9923-2412 0000-0002-9923-2412
著者名
Sawama, Yoshinari
キーワード等
heterocycles
Lewis acid catalyst
natural products
ortho-naphthoquinone methides
内容
This is the peer reviewed version of the following article: Aijima T., Komagawa S., Akai S., et al. Construction of Functionalized ortho-Naphthoquinone Methides via Site-Selective Ring Opening of 1-Siloxy-1,4-epoxy-1,4-dihydronaphthalenes. Advanced Synthesis and Catalysis 365, 3981 (2023), which has been published in final form at https://doi.org/10.1002/adsc.202300968. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
抄録
1-Siloxy-4-(benzyloxy)methyl-1,4-epoxy-1,4-dihydronaphthalenes, generated from benzynes and furans, underwent automatic site-selective ring opening because of the synergetic effect of the steric strain of the 1,4-epoxy moiety and the electron-donating ability of the siloxy group on the acetal structure to afford the precursors of ortho-naphthoquinone methides (o-NQMs). Subsequent Lewis acid-facilitated o-NQM formation and annulation with olefins afforded multi-fused heterocycles. Notably, the consecutive hexacyclic skeleton of rubioncolin B was constructed via solvent-dependent regioselective annulation of naphthofuran derivatives.
出版者
John Wiley and Sons Inc
収録物名
Advanced Synthesis and Catalysis
巻(号)
365(22)
ページ
3981-3986
刊行年月
2023-11-21
言語
英語
ハンドルURL
https://hdl.handle.net/11094/93212
PISSN
16154150
eISSN
16154169
関連情報 (isVersionOf)
DOI (出版社版)
https://doi.org/10.1002/adsc.202300968
アクセス権
open access
権利情報
© 2023 Wiley-VCH GmbH.
出版タイプ
Accepted Manuscript
カテゴリ
学術雑誌論文 Journal Article