Residual protic solvents CHCl3 (��=7.26 ppm) and CH3OH (��=3.30) were used as BAY 734506 the internal reference. 13C NMR spectra were recorded in CDCl3 or CD3OD at 50 MHz on a Bruker AC-200 and 150 MHz on a Bruker AC-600 spectrometer, using the central resonance of CDCl3 (��=77.16 ppm) as the internal reference. Infra-red spectra were recorded on a Perkin-Elmer 983G machine. Mass spectra were obtained on a Micromass Quattro Ultima (LC-ESI/APCI Triple Quadrupole Mass Spectrometer) at the chemistry department, McMaster University. The following ionization techniques were used: electron ionization (EI), and electrospray (ES). Melting points were determined on a Reichert hot stage apparatus. Optical rotations were recorded on a Perkin-Elmer (241 MC Polarimeter, ��=589, Na lamp).

Pramanicin (PMC) and pramanicin A (PMC-A) were prepared as described previously [20]. Flash column chromatography was carried out on silica gel (SILICA GEL 60). Thin layer chromatography (TLC) was performed on pre-coated silica plates (ALUGRAM SIL G/UV254) and visualized by UV, vanillin or ceric ammonium nitrate solution. Aqueous solutions were saturated unless otherwise specified. The ratio of solvents in mixtures refers to the volumes used. All reactions were carried out under a nitrogen or argon atmosphere in oven-dried glassware, which was cooled under a continuous stream of nitrogen immediately prior to use unless otherwise stated. THF was distilled from sodium benzophenone ketyl, CH2Cl2 and toluene from calcium hydride, and EtOAc from potassium carbonate. Other solvents and reagents were used as supplied.

3-Tetradecanoyl-1-vinylpyrrolidin-2-one (2) Freshly distilled N-vinylpyrrolidin-2-one (1) (0.96 mL, 9 mmol) was added to NaH (1.44 g, 36 mmol) in refluxing THF (15 mL). The mixture was stirred for 30 min at 90��C, and then ethyl myristate (4.3 mL, 10.3 mmol) was added. After 3 h, the solution was warmed to room temperature, quenched with saturated aqueous NH4Cl, and extracted with ether. The extracts were dried (Na2SO4), filtered, and concentrated. The resulting solid was dissolved in CH2Cl2, filtered and concentrated, and purified by chromatography (CH2Cl2/EtOAc, 11) to yield 2 as white crystals (3.54 g, 82%): mp 39�C40��C; IR (film) 2920, 2851 (C-H, str.), 1685, 1637 (C=O, str.), 1459 (C=C, bend.), 1391, 861 cm?1; 1H NMR (CDCl3, 200 MHz) �� 7.01 (1H, dd, 3J=9.0, 3J=16.

0, NCH=CH2), 4.46 (2H, m, NCH=CH2), 3.68 (1H, dd, 3J=9.0, 3J=6.0, COCHCO), 3.54 (1H, ddd, 2J=9.0, 3J=8.5, 3J=5.5, CH2N), 3.47 (1H, ddd, 2J=9.0, 3J=8.5, 3J=5.7, CH2N), 3.01 (1H, m, CH2CH2CO), 2.68 (1H, m, CH2CH2CO), 2.67 (1H, dddd, 2J=13.8, 3J=5.7, 3J=8.5, 3J=6.0, CH2CH2N), 2.12 (1H, dddd, 2J=13.6, 3J=8.5, 3J=9.0, 3J=5.5, CH2CH2N), 1.57 (2H, m, CH2CH2CO), 1.24 (20H, m, Brefeldin_A C10H20), 0.87 (3H, t, 2J=6.7, CH3CH2); 13C NMR (CDCl3, 50 MHz); �� 204.