A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate
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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.
Original language | English |
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Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 11 |
Pages (from-to) | 4400-4403 |
ISSN | 0022-3263 |
DOIs | |
Publication status | Published - 2009 |
- Former Faculty of Pharmaceutical Sciences
Research areas
ID: 13087220