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aSchool of Chemical Science and Technology, Yunnan University, P. R. China
bSchool of Chemical Science and Technology, Yunnan University, Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education), Kunming, P. R. China E-mail: email@example.com, firstname.lastname@example.org Fax: +86871 65031633 Tel: +86871 65031633
A first asymmetric synthesis of the lycorine-type Amaryllidaceae alkaloid (−)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction as a powerful tool to construct the skeleton of the alkaloid on the basis of unsaturated β-ketoester and nitroalkene is reported. The sequence afforded a highly functionalized intermediate with three stereogenic centres with high diastereoselectivity (>20:1 dr) and high enantioselectivity (92% ee) in one step, which was converted into (−)-δ-lycorane in eight steps.
The residue was purified by flash silica 8 Please do not adjust margins Please do not adjust margins Please do not adjust margins gel chromatography (DCM/MeOH = 10/1) to give (−)-δ-lycorane (9 mg, 72%) as a white solid.
m.p.: 125-126 °C; [α] = -51.9, (c = 0.1, CHCl3);
IR (thin film, ν cm -1): 3551, 3477, 3414 , 1637, 1617, 619, 473;