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Efficient and practical synthesis of l-hamamelose

Title
Efficient and practical synthesis of l-hamamelose
Authors
Kim W.H.Kang J.-A.Lee H.-R.Park A.-Y.Chun P.Lee B.Kim J.Kim J.-A.Jeong L.S.Moon H.R.
Ewha Authors
정낙신
Issue Date
2009
Journal Title
Carbohydrate Research
ISSN
0008-6215JCR Link
Citation
vol. 344, no. 17, pp. 2317 - 2321
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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 NaIO 4, 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. © 2009 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.carres.2009.09.011
Appears in Collections:
약학대학 > 약학과 > Journal papers
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