Structure and Absolute Stereochemistry of the Epoxyquinol LL - ClOO 37 a and Related Metabolites from Streptomyces LL - C 10037

1.08, CHCl3). To a suspension of CuBr (13 mg, 0.1 mmol) in ether (1 mL) at 0 "C was added allylmagnesium bromide (2.2 mL, 0.48 mmol), followed by the above-obtained tosyl-triflate 15 in ether (3 mL), and the reaction mixture was stirred at the same temperature for 3.5 h. Then n-Bu2CuLi (1.4 mmol) in ether (3 mL) was introduced and the mixture was stirred at room temperature for 12 h. Usual workup followed by column chromatography gave 62 mg (58%) of 14. Preparation of L-Factor [ (4S,SS)-(+)-5-Hydroxy-4-decanolide] (16). Through a solution of 14 (130 mg, 0.58 mmol) in 5 mL of MeOH cooled in a dry ice-acetone bath was passed a slightly excess of ozone. To the resulting pale blue solution was added dimethyl sulfide (1 mL), and the reaction mixture was slowly warmed to room temperature. After evaporation of most of the solvent, the obtained crude aldehyde was dissolved in MeOH (5 mL) and treated with AgNO, (200 mg, 1.2 mmol) in H20 (3 mL) and KOH (140 mg, 2.4 mmol) in H20 (2 mL) at 0 "C for 0.5 h. At the end of the reaction the mixture was acidified with concentrated HCl and gently refluxed for 0.5 h. After removal of the insoluble substance by filtration through Celite, the filtrate was concentrated. The residue was poured into AcOEt and rinsed with saturated NaCl. Following solvent removal, the crude product was purified by column chromatography to give 83 mg (77%) of 16 as a colorless oil, which was crystallized in a refrigerator: mp 39-41 "C (lkWj mp 42-44