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Recent progress in the Total Synthesis of typical lignans Pusheng Wang 2012-11-10.

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Presentation on theme: "Recent progress in the Total Synthesis of typical lignans Pusheng Wang 2012-11-10."— Presentation transcript:

1 Recent progress in the Total Synthesis of typical lignans Pusheng Wang

2 Ligin ( 木质素 ) and Lignan ( 木酯素 ) 2 木质素( Ligin )是由四种醇单体(对香豆醇、 松柏醇、 5- 羟基松柏醇、芥子醇)形成的一 种复杂酚类聚合物。 木脂素( Lignan )是一类由两分子苯丙素衍 生物(即 C6-C3 单体)聚合而成的天然化合 物,多数呈游离状态,少数与糖结合成苷而 存在于植物的木部和树脂中,故而得名。通 常所指其二聚体,少数可见三聚体、四聚体。

3 Total synthesis of typical ligans in recent years 3

4 Part A | (-)-Podophyllotoxin and (-)-Picropodophyllin David B. Berkowitz, J. Org. Chem. 2000, 65,

5 Part A | (−)-Sacidumlignans B and D C. V. Ramana, J. Org. Chem. 2012, 77,

6 Part B | (-)-talaumidin Yoshiyasu Fukuyama, Tetrahedron Lett. 2006, 47,

7 Part B | (+)-Chicanine Yoshiyasu Fukuyama, Tetrahedron Lett. 2011, 52,

8 Examination of the Mitsunobu etherification 8

9 Part B | (+)-veraguensin Subrata Ghosh, Tetrahedron Lett. 2010, 51,

10 Part B | (+)-virgatusin Jeffrey S. Johnson, Chem. Commun. 2009,

11 Part B | (+)-Magnolone Ganesh Pandey, Tetrahedron Lett. 2010, 51,

12 Part B | (+)-wikstromol Michael Sefkow, Tetrahedron: Asymmetry 2001, 12,

13 Part C | (+/-)-Paulownin Steven R. Angle, J. Org. Chem. 2008, 73,

14 Part C | (-)-Wodeshiol Oee Sook Park, J. Chem. Sci. 2011, 123,

15 Part D | Carpanone Craig W. Lindsley, Org. Lett. 2008, 10,

16 Part E | Dibenzocyclooctadiene Robert S. Coleman, J. Org. Chem. 2005, 70,

17 Part E | Eupomatilones Robert S. Coleman, Org. Lett. 2002, 6, J. Org. Chem. 2007, 72,

18 Part E | Eupomatilones Robert S. Coleman, Org. Lett. 2002, 6,

19 Part E | Eupomatilones Robert S. Coleman, J. Org. Chem. 2007, 72,

20 Part E | (-)-Steganone Gary A. Molander, J. Am. Chem. Soc. 2000, 122,

21 Summary Main source of chirality: 21


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