Synthesis of trans-SCH-A

K. Csatayová; S. G. Davies; J. A. Lee; K. B. Ling; P. M. Roberts; A. J. Russell; J. E. Thomson

doi:10.1055/s-0030-1258077

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Synfacts 2010(10): 1096-1096
DOI: 10.1055/s-0030-1258077

Synthesis of Natural Products and Potential Drugs

Synthesis of trans-SCH-A

Contributor(s): Philip Kocienski
K. Csatayová, S. G. Davies*, J. A. Lee, K. B. Ling, P. M. Roberts, A. J. Russell, J. E. Thomson
University of Oxford, UK

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Publication History

Publication Date:
22 September 2010 (online)

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Significance

trans-SCH-A is a melanin-concentrating hormone receptor antagonist with potential use for the treatment of obesity. The synthesis depicted (eight steps, 25% overall yield) features a stereodivergent cyclopropanation of the allyl carbamate A ¹, which reacts with Zn(CH₂I)₂ to give the syn-cyclopropane C (77% yield, dr = 99:1) or with CF₃CO₂ZnCH₂I to give the anti-cyclopropane B (90% yield, dr > 99:1).