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A Flexible and Divergent Strategy to Flavonoids with a Chiral A‑Ring Featuring Intramolecular Michael Addition: Stereoselective Synthesis of (+)-Cryptocaryone, (+)-Cryptogione F, and (+)-Cryptocaryanones A and B, as Well as (+)-Cryptochinones A and C
journal contribution
posted on 2018-03-19, 00:00 authored by Xiaojing Liu, Junhao Jia, Yuanliang Jia, He Gu, Jingwen Luo, Xiaochuan ChenA flexible strategy
has been developed to synthesize divergent
flavonoids bearing a chiral A-ring. As two key steps, the coupling
via a boron-mediated aldol condensation and the cyclization via a
highly stereoselective intramolecular Michael addition of 1,3-diketone
proceed under mild conditions; thus, the chiral flavonoids bearing
C-7 oxy functional groups or olefinic bonds are both easily accessible.
Using this approach, the first synthesis of (+)-cryptogione F, (+)-cryptocaryanone
B, and (+)-cryptochinones A and C, as well as stereoselective synthesis
of (+)-cryptocaryone and (+)-cryptocaryanone A, were achieved from
2-deoxy-d-ribose in high overall yields.
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cryptogionechiral flavonoidsCryptocaryanoneStereoselective Synthesisboron-mediated aldol condensationFlexibleFeaturingC -7 oxyFlavonoidcryptocaryoneCryptocaryoneCryptochinone2- deoxy-d-ribosecyclizationstrategycryptocaryanonediketonechiral A-ringIntramolecularapproachChiralcryptochinoneyieldstereoselective synthesisolefinic bondsstereoselective intramolecular Michael additionCryptogioneDivergent Strategy
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