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Studies toward the synthesis of Welwitindolinones Dong group at UT Austin Xuan Zhou May 08, 2013

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Page 1: Studies toward the synthesis of Welwitindolinonesgbdong.cm.utexas.edu/seminar/old/Study towards... · Studies toward the synthesis of Welwitindolinones Dong group at UT Austin Xuan

Studies toward the synthesis of

Welwitindolinones

Dong group at UT Austin

Xuan Zhou

May 08, 2013

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Contents

1.Background of Welwitindolinones

2. Studies toward synthesis of

Welwitindolinones

3. Total synthesis of Welwitindolinones

4.Acknowledgement

2

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Hapalindole-type natural products

Moore, R. E., et. al. J. Am. Chem. Soc. 1984, 106, 6456-6457

Baran, P. S ., et. al. J. Am. Chem. Soc. 2008, 130, 17938-179543

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Biosynthetic proposal of hapalindole –type alkaloids

Moore, R. E., et. al. J. Am. Chem. Soc. 1994, 116, 9935

Baran, P. S ., et. al. J. Am. Chem. Soc. 2008, 130, 17938-17954 4

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Welwitindolinone natural products

Garg, N. K., et. al. Angew. Chem. Int. Ed. 2012, 51, 3758-3765

Blue green alga

5

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Structure analysis of N-Methylwelwitindolinone C

isothiocyanate

Synthesis challenge

• Bicyclo[4.3.1]-decane ring system

• Contains four stereogenic centers

• Highly substitute C11-C12-C13 array

• Sensitive vinyl chloride, bridgehead

isothiocyanate, gem-dimethyl substituent

Biological activity:Exhibit biological activity against drug-

resistant cancer cells.

Garg, N. K., et. al. Angew. Chem. Int. Ed. 2012, 51, 3758-37656

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Konopelski’s synthesis to NMWCI

Konopelski, J. P., et. al. synlett. 1998, 1105-11087

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Konopelski’s synthesis to NMWCI

Konopelski, J. P., et. al. Org.lett. 2001, 3,3001-30048

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Wood’s synthesis to NMWCI skeleton

Wood, J. L ., et. al. J. Am. Chem. Soc. 1999, 121, 6326-6327 9

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Wood’s synthesis to NMWCI skeleton

Wood, J. L ., et. al. J. Am. Chem. Soc. 1999, 121, 6326-632710

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Rawal’s synthesis to NMWCI skeleton

Rawal, V. H., et. al. Org.lett. 2005, 7,3421-3424 11

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Rawal’s synthesis to NMWCI skeleton

Rawal, V. H., et. al. Org.lett. 2005, 7,3421-342412

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Simpkins’s work to NMWCI skeleton

Simpkings,N.S, et. al. Org.lett. 2005, 7,3421-3424 13

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Funk’s work to NMWCI skeleton

Funk,P. L ., et. al. J. Am. Chem. Soc. 2002, 124, 754-755

Funk,R.L, et. al. Org.lett. 2006, 8,2643-2645

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Funk’s work to NMWCI skeleton

Funk,P. L ., et. al. J. Am. Chem. Soc. 2006, 128, 4946-494715

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Funk’s work to NMWCI skeleton

1 was converted to 11 through 18 steps

Funk,R.L, et. al. Org.lett. 2006, 8,2643-264516

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Shea’s work to NMWCI skeleton

Shea,K.J, et. al. Org.lett. 2006, 8,5287-528917

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Shea’s work to NMWCI intermediate

Shea,K.J, et. al. Org.lett. 2009, 11,5330-533318

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Garg’s work to NMWCI skeleton

Garg,N.K, et. al. Org.lett. 2009, 11,2349-235119

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Martin’s work to NMWCI skeleton

Martin,S.F, et. al. Org.lett. 2009, 11,2349-235120

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Synthesis compound 1 through bis-allylic

alkylation strategy

Martin,S.F, et. al. Org.lett. 2009, 11,2349-235121

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Martin’s new synthesis route to NMWCI

skeleton

Martin,S.F, et. al. Org.lett. 2009, 11,2349-235122

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Martin’s formal synthesis of NMWCI

Martin,S.F, et. al. Org.lett. 2009, 11,2349-2351

Martin,S.F, et. al. Org.lett. 2012, 14,3834-3837 23

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Menendez’s work to NMWCI skeleton

Menendez,J.C, et. al. Org.Biomol.Chem. 2010,8,4521-452324

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Tang’s work to NMWCI skeleton

Tang,W, et. al. Angew.Chem.,Int.Ed. 2011, 50,1346-1348

Tang,W, et. al. Org.lett. 2012, 14,3756-3759725

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Tang’s work to NMWCI skeleton

Tang,W, et. al. Org.lett. 2012, 14,3756-3759726

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Rawal’s total synthesis of

N-methylwelwitindolinone D Isonitrile

Rawal,V. H., et. al. J. Am. Chem. Soc. 2011, 133, 5798-580127

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Rawal’s total synthesis of

N-methylwelwitindolinone D Isonitrile

28

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Rawal’s total synthesis of

N-methylwelwitindolinone D Isonitrile

Rawal,V. H., et. al. J. Am. Chem. Soc. 2011, 133, 5798-580129

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Garg’s total synthesis of

N-methylwelwitindolinone C isothiocyanate

Garg,N. K., et. al. J. Am. Chem. Soc. 2011, 133, 15797-1579930

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Garg’s total synthesis of

N-methylwelwitindolinone C isothiocyanate

31

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Garg’s total synthesis of

N-methylwelwitindolinone C isothiocyanate

Garg,N. K., et. al. J. Am. Chem. Soc. 2011, 133, 15797-1579932

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Acknowledgement

33


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