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Synfacts 2006(9): 0876-0876  
DOI: 10.1055/s-2006-942052
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of PNU-288034

Contributor(s): Philip Kocienski
C. V. Lu*, J. J. Chen, W. R. Perrault, B. G. Conway, M. T. Maloney, Y. Wang
Chemical Process Research and Development, Pfizer, Kalamazoo, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

PNU-288034 is an analogue of Zyvox (linezolide), a major new antibiotic launched in 2000. The key step is the Lewis acid catalyzed double Michael addition of 2,6-difluoroaniline to divinyl sulfone to give the thiomorpholine S,S-dioxide F. The same reaction using 85% phosphoric acid instead of AlCl3 gives F in 89% yield.