期刊
TETRAHEDRON
卷 71, 期 49, 页码 9313-9320出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.10.014
关键词
Negishi coupling; 3-Bromo-1,2-diketones; 3-Alkyl-1,2-diketones; Homocitric acid; Lycoperdic acid
资金
- Estonian Ministry of Education and Research [IUT19-32, IUT23-7]
- EU European Regional Development Fund [3.2.0101.08-0017]
Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methylalkoxycarbonyl- and 3(2-Boc-aminoethyl)-alkoxycarbonyl-1,2-cyclopentanediones homocitric and lycoperdic acid precursors. Homocitric and lycoperdic acids were synthesized using asymmetric oxidation with the Ti(OiPr)(4)/tartaric ester/tBuOOH complex in two steps from the obtained precursors. (C) 2015 Elsevier Ltd. All rights reserved.
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