Synthesis of the aglycon of aspafiliosides E and F via a spiroketal-forming cascade |
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| Authors: | Jing-Jing Wu Yong Shi Wei-Sheng Tian |
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| Institution: | CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China |
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| Abstract: | A facile synthesis of C17α-OH-tigogenin, the aglycon of aspafiliosides E and F, is described. The crucial step is the spiroketal-forming cascade, which forms the rings EF in one step and provides a new strategy for spiroketal ring closure in steroidal sapogenins and other substrates. This synthesis minimizes redundant oxidation-reduction manipulations of previous syntheses. |
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| Keywords: | Aspafilioside Spiroketal formation Pennogenin Dihydroxylation Synthesis |
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