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Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings.

ABSTRACT: Here we describe the diastereoselective synthesis of (5r,8r)-1,9-diazadispiro[4.2.4⁸ .2⁵ ]tetradecatrienes via domino double spirocyclization of N-arylamide derivatives. This reaction can serve as a fast way to synthesize diazadispirocycles, which are found in the core structures of bioactive natural products. Product diversification via Suzuki-Miyaura cross coupling and application to the synthesis of 1-oxa-9-azadispiro[4.2.4⁸ .2⁵ ]tetradecatrienes were also conducted.

SUBMITTER: Yokoe H

PROVIDER: S-EPMC7756633 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings.

Yokoe Hiromasa H Mizumura Yuka Y Sugiyama Kana K Yan Kejia K Hashizume Yuna Y Endo Yuto Y Yoshida Sae S Kiriyama Akiko A Tsubuki Masayoshi M Kanoh Naoki N

Chemistry, an Asian journal 20201023 24

Here we describe the diastereoselective synthesis of (5r,8r)-1,9-diazadispiro[4.2.48 .25 ]tetradecatrienes via domino double spirocyclization of N-arylamide derivatives. This reaction can serve as a fast way to synthesize diazadispirocycles, which are found in the core structures of bioactive natural products. Product diversification via Suzuki-Miyaura cross coupling and application to the synthesis of 1-oxa-9-azadispiro[4.2.48 .25 ]tetradecatrienes we ...[more]

PMID: 33029940

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