An efficient synthesis of pregaliellalactone and desoxygaliellalactone

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An efficient synthesis of pregaliellalactone and desoxygaliellalactone. / Furuseth, Eira Ruud; Larsson, Rikard; Blanco, Narda; Johansson, Martin H; Sterner, Olov.

In: Tetrahedron Letters, Vol. 55, No. 27, 2014, p. 3667-3669.

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Furuseth, Eira Ruud ; Larsson, Rikard ; Blanco, Narda ; Johansson, Martin H ; Sterner, Olov. / An efficient synthesis of pregaliellalactone and desoxygaliellalactone. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 27. pp. 3667-3669.

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TY - JOUR

T1 - An efficient synthesis of pregaliellalactone and desoxygaliellalactone

AU - Furuseth, Eira Ruud

AU - Larsson, Rikard

AU - Blanco, Narda

AU - Johansson, Martin H

AU - Sterner, Olov

PY - 2014

Y1 - 2014

N2 - A short and efficient total synthesis of rac-desoxygaliellalactone and (+)-desoxygaliellalactone, via the biosynthetic intermediate pregaliellalactone, is described. The synthesis was achieved in only three steps, for (+)-desoxygaliellalactone including an enantioselective alkyl propiolate addition to 4-pentenal, a palladium catalysed alkylative lactonisation and an intramolecular Diels-Alder cycloaddition. (C) 2014 Elsevier Ltd. All rights reserved.

AB - A short and efficient total synthesis of rac-desoxygaliellalactone and (+)-desoxygaliellalactone, via the biosynthetic intermediate pregaliellalactone, is described. The synthesis was achieved in only three steps, for (+)-desoxygaliellalactone including an enantioselective alkyl propiolate addition to 4-pentenal, a palladium catalysed alkylative lactonisation and an intramolecular Diels-Alder cycloaddition. (C) 2014 Elsevier Ltd. All rights reserved.

KW - Natural product

KW - Pregaliellalactone

KW - Desoxygaliellalactone

KW - Galiellalactone

KW - Enantioselective

KW - Biosynthesis

U2 - 10.1016/j.tetlet.2014.04.117

DO - 10.1016/j.tetlet.2014.04.117

M3 - Article

VL - 55

SP - 3667

EP - 3669

JO - Tetrahedron Letters

T2 - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -