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Total Synthesis of ( - )-Quinocarcin

Total Synthesis of ( - )-Quinocarcin. 李楠 2009.04.20. Stoltz. J. Am. Chem. Soc. , 2008 , 130 (51), 17270-17271 Myers. J. Am. Chem. Soc. , 2005 , 127 (48), 16796-16797 Zhu. J. Am. Chem. Soc. , 2008 , 130 (22), 7148-7152. inhibition of lung cancer activity against lymphocytic leukemia etc.

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Total Synthesis of ( - )-Quinocarcin

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  1. Total Synthesis of (-)-Quinocarcin 李楠 2009.04.20 Stoltz. J. Am. Chem. Soc., 2008, 130 (51), 17270-17271 Myers. J. Am. Chem. Soc., 2005, 127 (48), 16796-16797 Zhu. J. Am. Chem. Soc., 2008, 130 (22), 7148-7152

  2. inhibition of lung cancer activity against lymphocytic leukemia etc.

  3. install the labile oxazolidine ring intramolecular nucleophilic attack alkylation intermolecular condensation Pictet-Spengler reaction

  4. effectively obviated the regioselectivity

  5. mixture of two diastereomers (ratio 3/2) Strong nucleophile weak nucleophile

  6. E/Z = 8/1 deprotection under one-pot condition

  7. Stoltz's total synthesis of (-)-Quinocarcin

  8. auxiliary-controlled dipolar cycloaddition Screened Zn(OTf)2, Sc(OTf)3, and Sm(OTf)3, and none provided enamine 11 in greater than 40% yield.

  9. aryen annulation reaction

  10. Selectively condensed

  11. 10% overall yield 11 steps (shortest synthesis to date)

  12. Synthesis of Indolines and Isoquinolines via Aryne Annulation

  13. Baldwin规则：由于不同类型反应的分子轨道重叠不同，因此特定组合Baldwin规则：由于不同类型反应的分子轨道重叠不同，因此特定组合 的闭环反应具有相应得禁阻和允许性质。但含正离子和第二周期元素的 反应通常不符合该规则。 环中的原子个数，一般为3-8； 以exo和endo表示闭环时断键的位置，环内对应endo,环外对应exo; 以tet,trig和dig表示反应中亲电碳的杂化状态，tet对应sp3杂化，trig对应 sp2杂化，dig对应sp杂化。 例：

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