Concise synthesis of chafurosides A and B.
The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from beta-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.
Furuta
Takumi
T
School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Nakayama
Miho
M
Suzuki
Hirotaka
H
Tajimi
Hiroko
H
Inai
Makoto
M
Nukaya
Haruo
H
Wakimoto
Toshiyuki
T
Kan
Toshiyuki
T
D047309:Flavones / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013662:Tea / Q000737:chemistry
C510948:3,4,11-trihydroxy-2-(hydroxymethyl)-8-(4-hydroxyphenyl)-3,4,4a,11b-tetrahydro-2H,10H-pyrano(2',3'-4,5)furo(3,2-g)chromen-10-one; D047309:Flavones; D006576:Heterocyclic Compounds, 4 or More Rings; D007659:Ketones; D013662:Tea