Asymmetric Synthesis of Sappanin-Type Homoisoflavonoids
- Authors
- Lee J.; Kwon S.; Seo S.-Y.
- Issue Date
- May-2020
- Publisher
- Wiley-VCH Verlag
- Keywords
- asymmetric synthesis; chroman-4-one; homoisoflavonoid; natural products; sappanin
- Citation
- Asian Journal of Organic Chemistry
- Journal Title
- Asian Journal of Organic Chemistry
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/45691
- DOI
- 10.1002/ajoc.202000097
- ISSN
- 2193-5807
- Abstract
- Homoisoflavanones, 3-benzylchroman-4-ones, which are naturally occurring sappanin-type homoisoflavonoids, possess a 16-carbon skeleton and a single chiral center. In this paper, we present various asymmetric synthesis of homoisoflavanones that have been developed. The first approach is a lipase-catalyzed desymmetrization of 2-benzylpropane-1,3-diol and its diacetate. Three approaches for the synthesis of an optically active 3-benzylchroman-4-one are asymmetric protonation of the silyl enol ether derived from a racemic homoisoflavanone, iridium-catalyzed asymmetric hydrogenation of α-phenoxymethylcinnamic acid, and Evans asymmetric aldol reaction. Recently, our group performed Noyori ruthenium-catalyzed asymmetric transfer hydrogenation with dynamic kinetic resolution, followed by alcohol oxidation of 3-benzylchroman-4-ol. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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