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Article

Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One

by
Kazuhiro Higuchi
*,
Kazunori Matsumura
,
Takafumi Arai
,
Motoki Ito
and
Shigeo Sugiyama
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(1), 102; https://doi.org/10.3390/molecules27010102
Submission received: 29 November 2021 / Revised: 15 December 2021 / Accepted: 22 December 2021 / Published: 24 December 2021
(This article belongs to the Special Issue Heterocyclic and Organometallic Chemistry: Theme Issue in Honor of Prof. Daniel Comins’ Great Contribution)
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Abstract

Propellanes are polycyclic compounds in which tricyclic systems share one carbon–carbon single bond. Propellane frameworks that consist of larger sized rings are found in a variety of natural products. As an approach to the stereoselective synthesis of the propellane framework, one of the efficient methods is forming several rings in a single operation. Lapidilectine B (1) is composed of a propellane framework and was synthesized through the oxidative cyclization of trisubstituted alkenes. When the alkene with an ester moiety was treated with N-iodosuccinimide (NIS), iodocyclization proceeded to give the cyclic carbamate. On the other hand, when PhI(OAc)2 was allowed to react in the carboxyl form, a furoindolin-2-one structure corresponding to the A-B-C ring of lapidilectine B (1) was produced. Furthermore, when Pd(OAc)2 catalyst was used for cyclization under oxidative conditions, the product yield was improved.
Keywords: furoindolin-2-one; lapidilectine B; oxidative cyclization furoindolin-2-one; lapidilectine B; oxidative cyclization
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MDPI and ACS Style

Higuchi, K.; Matsumura, K.; Arai, T.; Ito, M.; Sugiyama, S. Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One. Molecules 2022, 27, 102. https://doi.org/10.3390/molecules27010102

AMA Style

Higuchi K, Matsumura K, Arai T, Ito M, Sugiyama S. Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One. Molecules. 2022; 27(1):102. https://doi.org/10.3390/molecules27010102

Chicago/Turabian Style

Higuchi, Kazuhiro, Kazunori Matsumura, Takafumi Arai, Motoki Ito, and Shigeo Sugiyama. 2022. "Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One" Molecules 27, no. 1: 102. https://doi.org/10.3390/molecules27010102

APA Style

Higuchi, K., Matsumura, K., Arai, T., Ito, M., & Sugiyama, S. (2022). Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One. Molecules, 27(1), 102. https://doi.org/10.3390/molecules27010102

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