Stereoselective synthesis of L-733,060

A Concise Enantioselective Synthesis of (+)-L-733,060 and (+)-T-2328 via Sequential Proline Catalysis

“…19 [α] D 25 +29.0 (c 1.4, CHCl3); IR (CHCl3, cm -1 ): υmax 700,1021,1049,1169,1250,1369,1391,1498,1513,1692,2977,3341; 1 H NMR (200 MHz, CDCl3): δ 1.41 (s, 9H), 2.83-2.96 (m, 2H), 4.87 (br s, 1H), 5.17 (br s, 1H), 7.26-7.34 (m, 5H), 9.73 (t, J = 1.7 Hz, 1H); 13 C NMR (50 MHz, CDCl3): δ 28. 3,39.9,49.9,79.9,126.3,127.7,128.8,135.2,155.0,193.3,199.8;Analysis: C14H19NO3 requires C,67.45;H,7.68;N,5.62;found: C,67.32;H,7.41;N,5.46%. All the data are in agreement with the reported values.…”

“…Yield: quantitative, colorless oil; [α] D 25 +35.9 (c 1.0, CHCl3), {lit. 3 [α] D 25 +38.3 (c 1.92, CHCl3)}; IR (CHCl3, cm -1 ): υmax 703, 1148, 1171, 1249, 1416, 1692, 2875, 2944, 2973, 1, 27.6, 28.3, 39.4, 59.2, 70.0, 79.9, 127.2, 128.3, 138.4, 155.4…”

Asymmetric Cycloaddition: An Efficient Synthesis of Enantiopure Isoxazolines Substituted with Carbohydrate Analogues

“…Moreover, isoxazolines have found textile industrial applications as dyes, photostabilizers, corrosion inhibitors, and agrochemicals . Therefore, the building up of a isoxazoline moiety invokes ever growing synthetic efforts .…”

Asymmetric Synthesis of (+)-L-733, 060 and (+)-CP-99, 994 Based on a New Chiral 3-Piperidinol Synthon

“…For example, (+)-L-733, 060 ( 1 ) and (+)-CP-99, 994 ( 2 ) are selective and potent neurokinin substance P receptor antagonists, which have been shown to possess potent antiemetic activity; febrifugine ( 3 ) and isofebrifugine ( 4 ) are well-known candidates of an antimalarial agent isolated from Chinese medicinal plants Dichroa febrifuga . The important bioactivities − associated both (+)-L-733, 060 ( 1 ) and (+)-CP-99, 994 ( 2 ) have stimulated the development of synthetic approaches. ,,, However, only two racemic total synthesis 1,4c of (±)-L-733, 060 and one asymmetric total synthesis of (+)-L-733, 060 have been reported very recently. 4e The success in the development of protected ( S )-malimide-based synthetic methodology from these laboratories 6 led us to consider the protected 3-hydroxyglutarimide 9 as a suitable multifunctional 3-hydroxypiperidine synthon.…”

“…Both diastereomers of 10 could be purified by recrystallization {major diastereomer, mp 165−166 °C, [α] 20 D −54.8° ( c 1.3, CHCl 3 ); minor diastereomer, mp 174.5−175.5 °C, [α] 20 D +31.7° ( c 0.9, CHCl 3 )}. The deoxygenative phenylation of 10 was first attempted using Tomooka's conditions 4c. Since the reaction was presumed to proceed via an N -acyliminium, 4c, which could be derived from both diastereomers of 10 , the diastereomeric mixture of 10 could be used as it was.…”