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By Harold H Trimm

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The SVOA compounds could not reliably be extracted from solids. The MDL values obtained for the less polar, longer chain VOA compounds, and the SVOA compounds are in the same range as those determined off of TDU tubes. Experimental Conditions Semivolatile Organic Extraction and Analysis Semivolatile Organic Analysis from Liquids Extraction The SVOA from liquids were extracted by placing 10 mL of water in a 10-mL glass headspace vial. Calibration standards were added to the vials along with a Twister stir bar extractor.

Reagents: (i) aq. HF (40%), MeOH, rt; (ii) Ac2O, pyridine, 0°C to rt; (iii) Lawesson’s reagent, PhMe, reflux; (iv) BrCH2CO2Et, MeCN, rt; (v) Ph3P, Et3N, MeCN, rt; (vi) K2CO3, MeOH, rt; (vii) I2, PPh3, imidazole, MeCN-PhMe (2:1), reflux; (viii) H2 (1 atm), PtO2, AcOH, rt; (ix) LiAlH4, THF, 0°C to rt; (x) MeSO2Cl, NEt3, CH2Cl2, 0°C to rt; (xi) Raney Ni, EtOH, reflux. In order to introduce the remaining stereogenic centres of the target system, the alkene bond of the bicyclic vinylogous urethane 39 needs to be reduced stereoselectively.

H−H COSY, HMQC, and HMBC)]. ). 54). The IR spectrum showed specific bands based on the C−O, C−N, aromatic C=C, and C−H bonds. The protonated molecular formula C37H47O2N2 was determined by exact FAB-MS spectrum. The elemental analysis confirmed the molecular formula C37H46O2N2. The 1H NMR spectrum showed signals based on a 3-guaiazulenyl group, signals based on two nonequivalent 4-[2(dimethylamino)ethoxy]phenyl groups, and a signal based on an ethylene part (>C=CH−). The 13C NMR spectrum exhibited 29 carbon signals, which could be assigned using HMQC and HMBC techniques.

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