Solid-phase synthesis of enantio-controlled lactic acid oligomers |
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| Authors: | Seong-Ho Kim Yong-Kyun Sim Bum-Tae Kim Yong Hwan Kim Yeong-Joon Kim Seongsoon Park Hyuk Lee |
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| Institution: | 1. Medicinal Chemistry Research Center, Korea research Institute of Chemical Technology, 141 Gajeong-ro, Yuseong-gu, Daejeon 305-600, Republic of Korea;2. Department of Chemical Engineering, Kwangwoon University, 447-1 Wolgye-dong, Nowon-gu, Seoul 139-701, Republic of Korea;3. Department of Chemistry, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea;4. Department of Chemistry, Center for NanoBio Applied Technology, Institute of Basic Sciences, Sungshin Women’s University, Seoul 136-742, Republic of Korea |
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| Abstract: | A synthetic method for lactic acid oligomers via solid-phase synthesis under mild reaction conditions with up to 99% yield is presented. The fine control of the chirality on each lactic acid unit of the oligomers was easily achieved by the substitution of (R)-THP-protected lactic acid (R)-2 by (S)-2 without alternating the procedure. The overall synthesis of the trimer and tetramer was completed in one and two days, respectively. Intramolecular cyclizations of enantio-controlled lactic acids were also attempted through the Yamaguchi macrolactonization or the Mitsunobu reaction. However, we were unable to isolate single cyclic oligomers but always obtained a mixture of cyclic oligomers. |
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