Synthesis of seco-psymberin/irciniastatin A: the discovery of a novel PhI(OAc)2 mediated cascade cyclization reaction |
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Authors: | Xianhai Huang Ning Shao Anandan Palani Robert Aslanian Alexei Buevich Cynthia Seidel-Dugan Robert Huryk |
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Affiliation: | Department of Chemical Research, Schering-Plough Research Institute, Kenilworth, NJ 07033, United States |
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Abstract: | The psymberin unsaturated ‘psymberate’ side chain 7 was synthesized in 7 steps (36% yield) with good diastereoselectivity using commercially available starting material to control the stereochemistry at C4 and C5. The synthesis of seco-psymberin was completed in an efficient manner based on a CuI mediated coupling reaction between vinyl iodide 8 and ‘psymberamide’ 7. In an attempt to synthesize natural psymberin from the seco-intermediate, a novel PhI(OAc)2 mediated cascade ring closing reaction was discovered. A possible mechanistic pathway for the formation of the ring closing product was presented. |
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Keywords: | Total synthesis seco-Psymberin &lsquo Psymberate&rsquo side chain (Diacetoxyiodo)benzene Oxidative cyclization |
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