This article describes a concise synthesis of cardiotonic steroids oleandrigenin () and its subsequent elaboration into the natural product rhodexin B () from the readily available intermediate () that could be derived from the commercially available steroids testosterone or DHEA three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin () in 12 steps (LLS) and a 3.1% overall yield from . The synthetic oleandrigenin () was successfully glycosylated with l-rhamnopyranoside-based donor using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B () in a 66% yield (two steps).
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8582021 | PMC |
| http://dx.doi.org/10.1021/acs.joc.1c00985 | DOI Listing |
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