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A versatile method for the solid-phase synthesis of oxazolidinones is described. An appropriate 1,2-diol is attached to immobilized sulfonyl chloride, resulting in the selective activation of one of the alcohol functions. The subsequent reaction of the other alcohol group with an isocyanate, followed by a base-promoted cycloelimination gives an oxazolidinone. By proper choice of isocyanates, functionalities can be introduced which are essential for antibiotic activity.
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Holte et al. (2001) studied this question.
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