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Diastereodivergent Synthesis of Syn- and Anti-9-Hydroxyhomoisoflavanone and its Application to the Total Syntheses of (+/-)-Homoferrugenone and (+/-)-Portulacanone F
- Authors
- Lee, Sanha; Kwon, Sangil; Hur, Joonseong; Seo, Seung-Yong
- Issue Date
- Oct-2022
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Aldol reaction; Diastereoselectivity; Hydrides; Protonation; Structure elucidation; Total synthesis
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.364, no.20, pp.3489 - 3495
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 364
- Number
- 20
- Start Page
- 3489
- End Page
- 3495
- ISSN
- 1615-4150
- Abstract
- The diastereodivergent synthesis of synand anti-9-hydroxyhomoisoflavanone from various chromones and carbaldehydes is described. The synthetic approaches involving the reductive aldol reaction or the Morita-Baylis-Hillman reaction followed by syn-selective 1,4-reduction provide both diastereomers of beta-hydroxy chroman-4-ones in 51-98% yield with anti (2 : 1-16 : 1 anti/syn) or 22-80% yield with syn (5 : 1-48 : 1 syn/anti) diastereo-selectivity. The ambiguity surrounding the stereochemistry of two 9-hydroxyhomoisoflavanones, homoferrugenone and portulacanone F was elucidated via the first total syntheses.
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Related Researcher
- Seo, Seung Yong
- Pharmacy (Dept.of Pharmacy)