Tetrahedron p. 10239 - 10252 (1997)
Update date:2022-08-02
Topics: Total synthesis Optically active Aromatic Enantiomeric pair FR980482
Yoshino, Toshiharu
Nagata, Yuriko
Itoh, Etsuko
Hashimoto, Masaru
Katoh, Tadashi
Terashima, Shiro
The synthesis of the aromatic segment 4 was achieved starting from commercially available 5-hydroxyisophthalic acid (6) by utilizing Claisen rearrangement of 9, bromolactonization of 12, and modified Curtius rearrangement of 16 as the key steps. Furthermore, the optically active aliphatic segments 5 and ent-5 were synthesized in enantiomerically pure forms starting with natural (2R, 3R)- and unnatural (2S, 3S)-diethyl tartrate (7 and ent-7), respectively: The synthetic scheme features epoxide formation of 26, nucleophilic epoxide opening of 27 with an azide anion, reduction of the azide function in 33 to an amine, and formation of the N-protected 1,3-oxazolidine 35.
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