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Volumn 46, Issue 7, 2007, Pages 1160-1163

Variable synthesis of the optically active thiotetronic acid antibiotics thiolactomycin, thiotetromycin, and 834-B1

Author keywords

Chirality transfer; Didesoxygenation; Epoxidation; Stereoselective synthesis; Vinyl epoxides

Indexed keywords

CATALYST ACTIVITY; OPTICAL PROPERTIES; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL); VINYL RESINS; VITAMINS;

EID: 34247254264     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603562     Document Type: Article
Times cited : (22)

References (59)
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    • 13: Thiopropionic acid (1.03 g, 11.4 mmol, 5.0 equiv) in CH 2Cl2 (40 mL) was added to AlMe3 (2.0M in heptane, 5.7 mL, 11 mmol, 5.0 equiv) in CH2Cl2 (40 mL) at -78°C over 25 min. The reaction mixture was allowed to warm to room temperature during 60 min and then recooled to -78°C. A solution of vinyl epoxide 4 (93% ee in this experiment; 1.0 g, 2.3 mmol) in CH 2Cl2 (40 mL) was then added over 40 min. The resulting mixture was slowly warmed to room temperature and stirred for 30 min. After the addition of NaOH (1M, 40 mL) and phase separation, the aqueous layer was extracted with CH2Cl2 (3 x 60 mL, The combined organic phases were washed with H2O (80 mL) and saturated Na/K tartrate solution (80 mL, dried over MgSO4, and concentrated under vacuum. The residue was chromatographed on silica gel eluent cyclohexane/ethyl ace
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    • The ee values of (+)-1, (+)-17, (+)-18, and (+)-19 varied somewhat (90-95%) because their precursors were derived from different samples of vinyl epoxide 4 and its α-ethyl analogue. The enantiopurity of these epoxides depended critically on the epoxidizing temperature and was not always the same.
    • The ee values of (+)-1, (+)-17, (+)-18, and (+)-19 varied somewhat (90-95%) because their precursors were derived from different samples of vinyl epoxide 4 and its α-ethyl analogue. The enantiopurity of these epoxides depended critically on the epoxidizing temperature and was not always the same.


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