We describe a concise enantioselective synthesis of the HIV-protease inhibitor nelfinavir (1) via a new route in which the key step is construction of the central optically active 1,2-amino alcohol framework via asymmetric bromocyclization of bisallylic amide with N-bromosuccinimide in the presence of a catalytic amount of ( S)-BINAP or ( S)-BINAP monoxide. The remaining alkene and bromo functionalities were used to install the requisite thioether and chiral perhydroisoquinoline units, respectively.

A new γ-butenolide glycoside, named styphnoloside A (1), was isolated from the root of Styphnolobium japonicum (L.) Schott (= Sophora japonica L.), together with saikoisoflavonoside A (2) and sophoraside A (3). The structure of 1 was characterized as puerol B 2"-O-neohesperidoside based on oneand two-dimensional (1D and 2D) NMR, MS, and electronic circular dichroism (ECD) spectral data. The absolute configuration of the aglycone moiety of 1 was assigned by comparing its experimental ECD spectrum with the calculated ECD spectrum.Styphnolobium japonicum (L.) Schott (= Sophora japonica L.) is a deciduous tree belonging to the Leguminosae family and is native to China. The bud, fruit and root are used in crude drugs known as "huai-gen" in Chinese. The dried flowers of S. japonicum are used in traditional Japanese medicine for anti-hemorrhagic, anti-hemostatic, and analgesic effects. 1,2 There have been few phytochemical investigations of the root of S. japonicum to date aside from our previously reported isolation and structural elucidation of several flavonoids 3,4 and butenolides. 5,6 In the current paper, we report the isolation, purification, and structure elucidation of a new γ-butenolide glycoside, styphnoloside A (1), together with two known compounds, saikoisoflavonoside A 7 (2) and sophoraside A 5,6 (3), from the root this plant.The roots were dried, extracted with methanol (MeOH) under reflux, and the organic solvent was removed by vacuum evaporation. The combined MeOH extract was suspended in water and partitioned with diethyl ether (Et2O), ethyl acetate (EtOAc) and n-butanol (n-BuOH) successively to yield the corresponding soluble layers. The n-BuOH soluble portion was separated by octadecyl-silyl (ODS) column chromatography into 16 fractions (Fr. 1 to 16). Fr. 2 was further subjected to ODS column