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Type: Journal article
Title: A concise route to branched erythrono-γ-lactones. Synthesis of the leaf-closing substance potassium (±)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate
Other Titles: A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium ()-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate
Author: Pedersen, D.
Robinson, T.
Taylor, D.
Tiekink, E.
Citation: Journal of Organic Chemistry, 2009; 74(11):4400-4403
Publisher: Amer Chemical Soc
Issue Date: 2009
ISSN: 0022-3263
Statement of
Daniel Sejer Pedersen, Tony V. Robinson, Dennis K. Taylor and Edward R. T. Tiekink
Abstract: A series of 1,2-dioxanes 3 were ring-opened with Co(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2-C-d-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.
Keywords: Plants; Plant Leaves; Sugar Acids; Lactones; Dioxanes; Biological Agents
Description: © 2009 American Chemical Society
RMID: 0020090761
DOI: 10.1021/jo900392y
Appears in Collections:Chemical Engineering publications

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