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

Hiromasa Yokoe; Yuka Mizumura; Kana Sugiyama; Kejia Yan; Yuna Hashizume; Yuto Endo; Sae Yoshida; Akiko Kiriyama; Masayoshi Tsubuki; Naoki Kanoh

doi:10.1002/asia.202001179

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

Chem Asian J. 2020 Dec 14;15(24):4271-4274. doi: 10.1002/asia.202001179. Epub 2020 Oct 23.

Authors

Affiliation

¹ Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.

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.

Keywords: cross coupling; cyclization; dearomatization; domino reactions; natural products.

Abstract

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