Efficient and practical synthesis of l-hamamelose
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- 作者：Won Hee Kim ; Jin-Ah Kang ; Hyung-Rock Lee ; Ah-Young Park ; Pusoon Chun ; Boeun Lee ; Jungsu Kim ; Jin-Ah Kim ; Lak Shin Jeong ; Hyung Ryong Moon
- 关键词：l-Hamamelose ; Chiral building block ; Crossed aldol reaction ; Johnson– ; Lemieux oxidation
- 刊名：Carbohydrate Research
- 出版年：2009
- 出版时间：23 November 2009
- 年：2009
- 卷：344
- 期：17
- 页码：2317-2321
- 全文大小：289 K
文摘
An efficient synthetic route of l-hamamelose was successfully accomplished starting from d-ribose. l-Hamamelose was synthesized in 42 % overall yield with six reaction steps via a stereoselective Grignard reaction, a stereoselective crossed aldol reaction and a controlled oxidative cleavage of the double bond of a vinyl diol compound. During the oxidative cleavage of the double bond of the vinyl diol compound with osmium tetroxide and NaIO4, an over-oxidative cleavage of α-hydroxyl aldehyde generated from ring opening of the first cleaved product, formyl lactol, did not occur, probably due to the stability of the lactol form. A plausible mechanism for the stereoselective crossed aldol reaction was suggested. The final target compound, l-hamamelose can play a very important role as a chiral building block in synthesizing a wide variety of enantiopure compounds.