| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345736 | Tetrahedron: Asymmetry | 2006 | 4 Pages |
Japonilure and its enantiomer, that is, (R)-(−)- and (S)-(+)-(5Z)-tetradecen-4-olide, have been synthesised in satisfactory overall yields using a highly convergent procedure. In situ prepared 1-decynylethylzinc was enantioselectively coupled to isopropyl 4-oxobutanoate in the presence of (S)- or (R)-BINOL. The alkoxy-ester intermediates obtained were cyclised to the corresponding substituted γ-lactones, carrying a triple bond in the side chain. Lindlar-hydrogenation of the latter yielded the target compounds.
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(R)-5-(Dec-1-ynyl)-dihydrofuran-2(3H)-oneC14H22O2Ee = 90%[α]D28=-6.0 (c 2.6, CHCl3)Absolute configuration: R
(R,Z)-5-(Dec-1-enyl)-dihydrofuran-2(3H)-oneC14H24O2Ee = 87%[α]D23=-61.1 (c 1.5, CHCl3)Absolute configuration: R
