Total synthesis of (−)-aplaminal by Buchwald–Hartwig cross-coupling of an aminal

Takayuki Ohyoshi; Kei Akemoto; Ayaka Taniguchi; Takuma Ishihara; Hideo Kigoshi

doi:10.1039/C9NJ04743C

Total synthesis of (−)-aplaminal by Buchwald–Hartwig cross-coupling of an aminal†

Takayuki Ohyoshi,

*^a Kei Akemoto,^a Ayaka Taniguchi,^a Takuma Ishihara^a and Hideo Kigoshi

*^a

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* Corresponding authors

^a Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571, Japan
E-mail: ohyoshi@chem.tsukuba.ac.jp, kigoshi@chem.tsukuba.ac.jp

Abstract

The concise total synthesis of an unusual alkaloid, aplaminal, has been accomplished. The synthetic feature is the Buchwald–Hartwig cross-coupling between a novel triazabicyclo[3.2.1]octane core and an aromatic bromide. The practicality of our approach provides aplaminal analogs and preliminary structure–cytotoxicity relationships of an aromatic moiety were achieved.

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https://doi.org/10.1039/C9NJ04743C

Submitted

17 Sep 2019

Accepted

05 Nov 2019

First published

06 Nov 2019

Download Citation

New J. Chem., 2019,43, 18442-18444

Article type

Letter

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Total synthesis of (−)-aplaminal by Buchwald–Hartwig cross-coupling of an aminal

T. Ohyoshi, K. Akemoto, A. Taniguchi, T. Ishihara and H. Kigoshi, New J. Chem., 2019, 43, 18442

DOI: 10.1039/C9NJ04743C

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Total synthesis of (−)-aplaminal by Buchwald–Hartwig cross-coupling of an aminal†

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Total synthesis of (−)-aplaminal by Buchwald–Hartwig cross-coupling of an aminal

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