Transcript Recent progress in the Total Synthesis of typical lignans

Recent progress in the Total
Synthesis of typical lignans
Pusheng Wang
2012-11-10
Ligin (木质素) and Lignan (木酯素)
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。
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Total synthesis of typical ligans in recent years
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Part A | (-)-Podophyllotoxin and (-)-Picropodophyllin
David B. Berkowitz, J. Org. Chem. 2000, 65, 847-860
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Part A | (−)-Sacidumlignans B and D
C. V. Ramana, J. Org. Chem. 2012, 77, 1566-1571
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Part B | (-)-talaumidin
Yoshiyasu Fukuyama, Tetrahedron Lett. 2006, 47, 3979-3983
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Part B | (+)-Chicanine
Yoshiyasu Fukuyama, Tetrahedron Lett. 2011, 52, 3005-3008
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Examination of the Mitsunobu etherification
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Part B | (+)-veraguensin
Subrata Ghosh, Tetrahedron Lett. 2010, 51, 6924-6927
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Part B | (+)-virgatusin
Jeffrey S. Johnson, Chem. Commun. 2009, 5135-5137
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Part B | (+)-Magnolone
Ganesh Pandey, Tetrahedron Lett. 2010, 51, 2975-2978
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Part B | (+)-wikstromol
Michael Sefkow, Tetrahedron: Asymmetry 2001, 12, 987-989
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Part C | (+/-)-Paulownin
Steven R. Angle, J. Org. Chem. 2008, 73, 6268-6278
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Part C | (-)-Wodeshiol
Oee Sook Park, J. Chem. Sci. 2011, 123, 327-330
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Part D | Carpanone
Craig W. Lindsley, Org. Lett. 2008, 10, 4097-4100
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Part E | Dibenzocyclooctadiene
Robert S. Coleman, J. Org. Chem. 2005, 70, 8932-8941
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Part E | Eupomatilones
Ar
In
Ar
O
Ar
HO
H
O
O
eupomatilones 4, 6
R2
R1
MeO
O
B(OR*)2
OMe
Ar
Ar
H
O
O
R3
R5
R4
eupomatilones
O
O
O
eupomatilones 1, 2, and 5
Robert S. Coleman, Org. Lett. 2002, 6, 4025-4028
J. Org. Chem. 2007, 72, 8724-8736
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Part E | Eupomatilones
Robert S. Coleman, Org. Lett. 2002, 6, 4025-4028
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Part E | Eupomatilones
Robert S. Coleman, J. Org. Chem. 2007, 72, 8724-8736
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Part E | (-)-Steganone
Gary A. Molander, J. Am. Chem. Soc. 2000, 122, 52-57
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Summary
Main source of chirality:
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