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Total synthesis of solanoeclepin A

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Presentation on theme: "Total synthesis of solanoeclepin A"— Presentation transcript:

1 Total synthesis of solanoeclepin A
何玉萍

2 a, Potato cyst nematode Globodera rostochiensis
a, Potato cyst nematode Globodera rostochiensis. b, Cysts on potato roots, which protect the nematodes until hatch stimulants produced by the host plant are present. c, Potato field affected by potato cyst nematodes.

3 stereoselective Simmon-Smith reaction Coupling reaction G E D based-induced intramolecular cyclization F C A B intramolecular Diels-Alder reaction

4 Meinwald rearrangement Sharpless 环氧化反应

5 Meinwald rearrangement
Pd(0)/PR3 (5 mol %), Bi(OTf)3·xH2O (0.1 mol %), IrCl3·xH2O (1 mol %), and Er(OTf) (1 mol %) hydrgeon migration CrTPP(OTf), (1 mol %), CrTBPC(OTf ) , (1 mol %) alkyl migration

6 J . Am. Chem. Soc.,1958, 80, 6303 Tetrahedron Letters, 2003, 44 , 7687 J. Am. Chem. Soc. 2004, 126, 9554 Chem. Commun., 2009, 1255

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8 Simmons–Smith reaction
J. Am. Chem. Soc. Vol. 120, No. 46, 1998,11945

9 mechanism J. Org. Chem., Vol. 40, No. 7, 1975

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11 mechanism

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13 Hiyama Coupling

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16 配体交换 扭转 消除

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19 solanoeclepin A


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