
doi: 10.1021/jo030355b
pmid: 15104474
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.
Sphingosine, Organometallic Compounds, Serine, Stereoisomerism, Ketones, Amides
Sphingosine, Organometallic Compounds, Serine, Stereoisomerism, Ketones, Amides
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