Total synthesis of (−)-dysiherbaine, a novel neuroexcitotoxic amino acid

Author:

Sasaki Makoto,Koike Tatsuki,Sakai Ryuichi,Tachibana Kazuo

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference12 articles.

1. Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112–4116.

2. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866–876, and references cited therein.

3. Sasaki, M.; Maruyama, T.; Sakai, R.; Tachibana, K. Tetrahedron Lett. 1999, 40, 3195–3198.

4. A first total synthesis of dysiherbaine (1) has been achieved by the Iwabuchi and Hatakeyama group of Nagasaki University. They completed the total synthesis by a cross-coupling based strategy very similar to ours and established the absolute configuration of dysiherbaine as shown in structure 1: Masaki, H.; Maeyama, J.; Kamada, K.; Iwabuchi, Y.; Hatakeyama, S. In 41th Symposium on the Chemistry of Natural Products; Symposium papers, 1999; pp. 13–18. Very recently, the second total synthesis has been reported: Snider, B. B.; Hawryluk, N. A. Org. Lett. 2000, 2, 635–638.

5. Palladium(0)-catalyzed cross-coupling reaction of 3 with aryl halides has been successfully used for the preparation of various amino acids: Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397–3404.

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