10.1021/acs.orglett.8b00479.s001
Xiaojing Liu
Xiaojing
Liu
Junhao Jia
Junhao
Jia
Yuanliang Jia
Yuanliang
Jia
He Gu
He
Gu
Jingwen Luo
Jingwen
Luo
Xiaochuan Chen
Xiaochuan
Chen
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
American Chemical Society
2018
cryptogione
chiral flavonoids
Cryptocaryanone
Stereoselective Synthesis
boron-mediated aldol condensation
Flexible
Featuring
C -7 oxy
Flavonoid
cryptocaryone
Cryptocaryone
Cryptochinone
2- deoxy-d-ribose
cyclization
strategy
cryptocaryanone
diketone
chiral A-ring
Intramolecular
approach
Chiral
cryptochinone
yield
stereoselective synthesis
olefinic bonds
stereoselective intramolecular Michael addition
Cryptogione
Divergent Strategy
2018-03-19 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/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/6000185
A 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.