Stereospecific total synthesis of (−)-8-epi-hyperaspine |
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| Authors: | Dawei Ma Wei Zhu |
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| Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China |
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| Abstract: | Condensation of protected δ-hydroxy-β-amino ester 7 with a β-keto ester provides vinylogous urethane 8, which is cyclized under the action of t-BuOK followed by decarboxylation to afford enone 12. Hydrogenation of 12 or its N,O-diprotected derivative 13 gives 2,6-cis-disubstituted piperdines. Using these intermediates, (−)-8-epi-hyperaspine is synthesized. |
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