TY - JOUR A1 - Enders, Dieter A1 - Fronert, Jeanne A1 - Bisschops, Tom A1 - Boeck, Florian T1 - Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step JF - Beilstein Journal of Organic Chemistry PY - 2012/// VL - 8 SP - 1112 EP - 1117 SN - 1860-5397 DO - 10.3762/bjoc.8.123 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.8.123 KW - aldol reaction KW - asymmetric synthesis KW - organocatalysis KW - proline KW - smyrindiol N2 - The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed. ER -