- The structural revision and total synthesis of carambolaflavone a
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The synthesis of both enantiomers of carambolaflavone A, the antidiabetic and flavonoid C-glycoside, was achieved for the first time via a 12-longest-linear-step with 16% (l-fucose) and 11% (d-fucose) overall yields. Through the synthetic investigation, the adverse effect of 4A MS in Suzuki C-glycosylation was disclosed, the mechanism of hydrogen-bonded-phenol involved Suzuki C-glycosylation was clarified, and the authentic structure of carambolaflavone A was also determined.
- Wang, Yong,Liu, Miao,Liu, Lei,Xia, Jian-Hui,Du, Yu-Guo,Sun, Jian-Song
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p. 4111 - 4118
(2018/04/14)
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- Concise synthesis of chafurosides A and B
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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 β-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,Nakayama, Miho,Suzuki, Hirotaka,Tajimi, Hiroko,Inai, Makoto,Nukaya, Haruo,Wakimoto, Toshiyuki,Kan, Toshiyuki
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supporting information; experimental part
p. 2233 - 2236
(2009/10/02)
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