Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide
The Journal of Organic Chemistry2004Vol. 69(9), pp. 3233–3235
Citations Over TimeTop 17% of 2004 papers
Regina C. So, Rachel M. Ndonye, Douglas P. Izmirian, Stewart K. Richardson, Robyn L. Guerrera, Amy R. Howell
Abstract
Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.
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