[CH2:1]([S:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:18]([C:26](OC)=[O:27])(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C(=CC2C=CC=CC=2)C(O)=O)C=CC=CC=1.SC(C1C=CC=CC=1)C(O)=O>CN(C)C=O>[OH:27][C:26]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
To an ice cooled, stirred solution of dibenzyl sulfide (2.14 g, 0.01 m) in dried N,N-dimethylformamide was added sodium hydride (0.88 g, 0.022 mmol of a 60% suspension in mineral oil). The mixture was gradually heated to 60° C. (bath temperature), kept 2 hours and allowed to cool. Methyl benzoylformate (1.42 ml, 0.01 mmol) was then added and the mixture heated at 60° C. for 1 hour, cooled, added to a stirred ice-dilute hydrochloric acid-ether mixture, separated, the aqueous layer re-extracted 1 time with ether, and the combined organic layer washed 2 times with water, dried over sodium sulfate, filtered and concentrated to a residue. Chromatography on silica gel (1 time flush with 10% ethyl acetate/hexane followed by a careful chromatography with a methylene chloride/hexane mixture) yielded 50 mg. of product compound as a pale yellow-white crystalline material. M.S.: M+ =328; NMR: consistent, identical to the nmr spectrum of material prepared from α-phenylcinnamic acid and α-mercaptophenylacetic acid via Michael addition and ring closure. ##STR28##
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