Asymmetric synthesis of D-(E)-2-amino-5-phosphono-3-pentenoic acid (APPA) by using a chiral auxiliary

Article abstract of DOI:10.1271/bbb.60.680

The synthesis of D-2-amino-5-phosphono-3-pentenoic acid (1) is reported. The key intermediate, a (2R,3S)-3-hydroxyallylglycine derivative (8), was prepared by the reaction of (5S)-3,6-dimethoxy-5-isopropyl-2,4-dihydropyrazine (2) and acrolein in the presence of chlorotitanium tris(diethylamide). The transformation of 8 into 1 via allylic alcohol 11 was carried out by following the reported route.

Full text of DOI:10.1271/bbb.60.680

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Asymmetric Synthesis of D-(E)-2-Amino-5-
phosphono-3-pentenoic Acid (APPA) by Using a Chiral
Auxiliary
Masashi Fukuaria, Itsuo Ichimotoa & Mitsunori Kirihataa
a Department of Applied Biochemistry, College of Agriculture, University of Osaka
Prefecture, Gakuen-cho, Sakai, Osaka 593, Japan
Published online: 12 Jun 2014.
To cite this article: Masashi Fukuari, Itsuo Ichimoto & Mitsunori Kirihata (1996) Asymmetric Synthesis of D-(E)-2-Amino-5-
phosphono-3-pentenoic Acid (APPA) by Using a Chiral Auxiliary, Bioscience, Biotechnology, and Biochemistry, 60:4,
680-682, DOI: 10.1271/bbb.60.680
To link to this article: http://dx.doi.org/10.1271/bbb.60.680
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