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All compounds exhibited spectral data consistent with their structures. Melting point,
IR, NMR (1H and 13C) and HRMS spectral data for some of the compounds follow.
Triester 10a: IR (neat): 2954, 1731, 1434, 1247, 1157, 1074, 756, 735 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.12-7.19 (m, 4 H), 4.45 (dd, J = 5.3, 9.2 Hz, 1 H), 3.74 (s, 3 H), 3.71 (s, 6 H), 3.71 (AB, J = 16.4 Hz, 1 H), 3.42 (AB, J = 16.4 Hz, 1 H), 2.74 (ABX, J = 5.3, 16.0 Hz, 1 H), 2.51 (ABX, J = 9.2, 16.0 Hz, 1 H). 13C NMR (100 MHz, CDCl3, DEPT): δ = 172.19 (C), 171.44 (C), 170.34 (C), 142.88 (CH), 138.96 (C), 127.56 (CH),
127.21 (CH), 124.25 (CH), 123.79 (CH), 64.31 (C), 52.96 (Me), 52.63 (Me), 51.74 (Me),
46.42 (CH), 39.28 (CH2), 36.24 (CH2). HRMS (ESI): m/z [M + Na+] calcd for C16H18O6Na: 329.1001; found: 329.0996.
Ketoester 11d: mp 114-117 °C. IR (neat): 2986, 1742, 1686, 1597, 1233, 750 cm-1. 1H NMR (400 MHz, CDCl3): δ = 8.05 (dd, J = 1.2, 8.4 Hz, 2 H), 7.61 (t, J = 7.6 Hz, 1 H), 7.50 (t, J = 7.6 Hz, 2 H), 7.22-7.26 (m, 3 H), 7.12-7.15 (m, 1 H), 4.56 (t, J = 6.8 Hz, 1 H), 4.36 (q, J = 7.2 Hz, 2 H), 3.77 (AB, J = 16.0 Hz, 1 H), 3.71 (d, J = 6.8 Hz, 2 H), 3.58 (AB, J = 16.0 Hz, 1 H), 1.33 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3, DEPT): δ = 197.37 (C), 168.52 (C), 141.01 (C), 137.95 (C), 136.34 (C), 133.62 (CH),
128.77 (CH), 128.22 (CH), 128.19 (CH), 127.90 (CH), 124.58 (CH), 123.60 (CH), 118.90
(C), 63.18 (CH2), 55.03 (C), 47.84 (CH), 42.92 (CH2), 40.83 (CH2), 13.96 (Me). HRMS (ESI): m/z [M + Na+] calcd for C21H19NO3Na: 356.1263; found: 356.1258.
Sulfone 11e: mp 125-127 °C. IR (neat): 3067, 2952, 1733, 1684, 1596, 1581, 1447, 1308, 1145,
749, 689 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.84-7.89 (m, 4 H), 7.54-7.58 (m, 2 H), 7.42-7.47 (m, 4 H), 7.03-7.09 (m, 3
H), 6.94-6.97 (m, 1 H), 4.86 (dd, J = 2.8, 8.8 Hz, 1 H), 3.89 (AB, J = 17.0 Hz, 1 H), 3.78 (AB, J = 17.0 Hz, 1 H), 3.70 (s, 3 H), 3.47 (ABX, J = 2.8, 17.6 Hz, 1 H), 3.33 (ABX, J = 8.8, 17.6 Hz, 1 H). 13C NMR (100 MHz, CDCl3, DEPT): δ = 197.44 (C), 167.78 (C), 142.21 (C), 138.58 (C), 136.81 (C), 136.70 (C),
134.26 (CH), 133.48 (CH), 130.48 (CH), 128.78 (CH), 128.76 (CH), 128.18 (CH), 127.82
(CH), 127.42 (CH), 123.96 (CH), 82.49 (C), 53.30 (Me), 45.35 (CH), 41.18 (CH2), 37.99 (CH2). HRMS (ESI): m/z [M + Na+] calcd for C25H22O5NaS: 457.1080; found: 457.1074.
Spirodione 13: mp 95-98 °C. IR (neat): 2923, 1734, 1704, 1595, 1277, 1238, 751, 732 cm-1. 1H NMR (400 MHz, CDCl3): δ = 8.02-8.06 (m, 1 H), 7.95-7.98 (m, 1 H), 7.82-7.89 (m, 2 H), 7.14-7.27 (m, 4
H), 4.22 (dd, J = 6.2, 9.3 Hz, 1 H), 3.35 (AB, J = 16.2 Hz, 1 H), 3.34 (s, 3 H), 3.28 (AB, J = 16.2 Hz, 1 H), 2.89-2.92 (m, 2 H). 13C NMR (100 MHz, CDCl3, DEPT): δ = 202.56 (C), 201.71 (C), 172.54 (C), 143.12 (CH), 141.86 (C), 141.73 (C),
139.58 (CH), 135.78 (CH), 135.65 (CH), 127.95 (CH), 127.60 (CH), 124.40 (CH), 123.60
(CH2), 123.47 (CH), 123.32 (CH), 61.81 (C), 51.58 (CH), 47.24 (CH2), 41.44 (CH2), 35.18 (CH2). HRMS (ESI): m/z [M + Na+] calcd for C20H16O4Na: 343.0946; found: 343.0954.
Lactam 16: mp 117-120 °C. IR (neat): 3235, 2982, 1721, 1651, 1485, 1367, 1265, 1224, 1015,
860, 732, 701 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.15-7.27 (m, 4 H), 6.04 (br s, 1 H), 4.18-4.24 (m, 1 H), 4.21 (q, J = 6.8 Hz, 2 H), 3.74 (ABX, J = 4.8, 13.2 Hz, 1 H), 3.43 (AB, J = 17.0 Hz, 1 H), 3.24 (ABX, J = 3.2, 13.2 Hz, 1 H), 3.02 (AB, J = 17.0 Hz, 1 H), 2.94 (ABX, J = 7.8, 15.6 Hz, 1 H), 2.53 (ABX, J = 6.4, 15.6 Hz, 1 H), 1.27 (t, J = 6.8 Hz, 3 H). 13C NMR (100 MHz, CDCl3, DEPT): δ = 174.97 (C), 173.55 (C), 143.72 (C), 139.52 (C), 127.58 (CH), 127.55 (CH),
124.46 (CH), 123.94 (CH), 61.53 (CH2), 53.15 (C), 46.84 (CH2), 45.54 (CH), 41.62 (CH2), 36.00 (CH2), 14.13 (Me). HRMS (ESI): m/z [M + Na+] calcd for C15H18NO3: 256.1287; found: 260.1291.
<A NAME="RD12107ST-9">9</A>
Representative Experimental Procedure: To a stirred solution of chloroester 1 (100.0 mg, 0.475 mmol) in DMF, were added dimethyl malonate (9a; 125.4 mg, 0.950 mmol) and Cs2CO3 (464.3 mg, 1.425 mmol) and the mixture was allowed to stir at r.t. for 3 h (TLC control).
The reaction mixture was then diluted with Et2O, washed with H2O followed by brine and dried over Na2SO4. Subsequent filtration, evaporation of the solvent and purification of the residue
by silica gel column chromatography using EtOAc-hexane (1:19) as eluent yielded the
triester 10a
[8]
(118.0 mg, 81%) as a viscous oil.
<A NAME="RD12107ST-10">10</A>
Crystal data for 11d: formula: C21H19NO3; unit cell parameters: a = 7.2791 (2), b = 12.4566 (4), c = 18.9233 (6) Å, β = 95.4010 (10)°; space group P2(1)/c; CCDC number 638873. Crystal data for 11e: formula: C25H22O5S; unit cell parameters: a = 12.8473 (3), b = 9.1054 (2), c = 18.5010 (4) Å, α = 90.00°, β = 95.8910 (10)°, γ = 90.00°; space group P2 (1)/c; CCDC number 638872. CCDC 638873 and CCDC 638872 contain the supplementary
crystallographic data for this paper. These data can be obtained free of charge from
The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
<A NAME="RD12107ST-11">11</A>
Meyer MD.
DeBernardis JF.
Hancock AA.
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1994,
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