Elsevier, Tetrahedron, 13(71), p. 2004-2012, 2015
DOI: 10.1016/j.tet.2015.02.008
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A concise synthesis of 28a-homolupane triterpenes and the corresponding saponins containing d-mannose, d-idose, d-arabinose, and l-rhamnose moieties was elaborated. The overall synthesis of the new triterpenes involved three linear steps starting from readily available 3-O-acetyl-betulinal: elongation of the carbon chain by Wittig reaction followed by enol ether hydrolysis and reduction (or oxidation) of the elongated aldehyde. Saponins were obtained by glycosylation of triterpenes with classical Schmidt donors.