Confirmation of the stereochemistry of two naturally occurring epimeric phenylpropanoids via synthesis: Elucidation of hitherto unknown full stereostructures |
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| Institution: | 1. College of Material Science and Engineering, Henan Polytechnic University, Jiaozuo 454000, People’s Republic of China;2. The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, People’s Republic of China;3. Department of Biology, Fred Wyszkowski Cancer Research Laboratory, Technion, Haifa 32000, Israel;5. Bioinformatics Knowledge Unit, The Lorry I. Lokey Interdisciplinary Center for Life Sciences and Engineering, Technion, Haifa 32000, Israel;4. Division of Integrated Life Science, Graduate School of Biostudies, Kyoto University, Kitashirakawa-Oiwake-cho, Sakyo-ku, Kyoto 606-8502, Japan;1. Department of Chemistry, National Institute of Technology, Agartala 799046, Tripura, India;2. Departament of de Química, Universitat de les lllesBalears, Crta. deValldemossa, 07122, Spain;3. Division of Chemistry & Biological Chemistry, Nanyang Technology University, Singapore 639798, Singapore;1. Dpto. Física Aplicada, Unidad Asociada IEM-CSIC, Facultad de Ciencias Experimentales, Universidad de Huelva, 21071 Huelva, Spain;2. Dpto. Química y Física Teóricas, Instituto de Estructura de la Materia, IEM-CSIC, Serrano 121, 28006 Madrid, Spain;3. Dpto. Química, UAM-I Purísima y Michoacán, s/n, 09340 México D.F., Mexico;4. Dpto. Ingeniería Civil, Cátedra de Química, E.U.I.T. Obras Públicas, Universidad Politécnica de Madrid, Spain |
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| Abstract: | Herein we report our efforts toward unequivocal assignment of the hitherto unknown absolute configurations of two naturally occurring phenylpropanoids from Abies delavayi and Abies fabri via a combination of chiral pool synthesis and single crystal X-ray analysis which also confirmed their previously reported gross structures with relative stereochemistry. Toward this end we have achieved the first stereodivergent syntheses of threo-(1R,2R)-(−)- and erythro-(1S,2R)-(+)-1-(4-hydroxyphenyl)-1-methoxy-2,3-propanediol. The synthetic threo-isomer was found to be identical to the naturally occurring threo-isomer, while the natural erythro-isomer was postulated to be the enantiomer of the synthetic erythro-isomer. |
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| Keywords: | Absolute configuration Natural products Chiral pool synthesis Single crystal X-ray analysis |
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