chen peihao 2019-4-21qigroup.nibs.ac.cn/.../03/...the-baran’s-lab-cph.pdf · ryan a shenvi....
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![Page 1: Chen Peihao 2019-4-21qigroup.nibs.ac.cn/.../03/...The-Baran’s-Lab-CPH.pdf · Ryan A Shenvi. Thomas Maimone. Tim Newhouse. PhD:2003-2008 . PhD:2004-2009. PhD:2005-2010. From Baran's](https://reader034.vdocuments.net/reader034/viewer/2022050201/5f5493810c185c10757a8f5c/html5/thumbnails/1.jpg)
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Chen Peihao 2019-4-21
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Ryan A Shenvi Thomas Maimone Tim Newhouse
PhD:2003-2008 PhD:2004-2009 PhD:2005-2010
From Baran's Lab
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Ryan A Shenvi Thomas Maimone Tim Newhouse
2010 Scripps 2012 UC Berkeley 2013 Yale
Now
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PhD IN Baran’s LAB
Baran,P.S; Shenvi,R. A;-JACS, 2006, 128,14028-14029.–Angew. Chem. Int. Ed. 2005, 44, 3714–3717.
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Ryan A Shenvi
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Isolation of Chartelline alkaloids
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Ryan A Shenvi
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Biosynthesis
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Ryan A Shenvi
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-JACS, 2006, 128,14028-14029.
–Angew. Chem. Int. Ed. 2005, 44, 3714–3717.8
Ryan A Shenvi
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Model Study
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Overall yield 0.072% 9
Ryan A Shenvi
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Baran: (+)-CortistatinoneRetrosynthesis:
Baran, P. J. Am. Chem. Soc. 2008, 130, 7241Baran, P. J. Am. Chem. Soc. 2011, 133, 8014
Challenges to be addressed:– control of all four A-ring stereocenters– oxidation of the unfunctionalized C19 and C8 centers– expansion of the B-ring– chemo-/stereoselective installation of the side chain
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Ryan A Shenvi
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Baran: A-Ring Functionalization
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Ryan A Shenvi
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Baran: B-Ring Expansion
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Ryan A Shenvi
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Baran: Isoquinoline Installation
Baran, P. J. Am. Chem. Soc. 2008, 130, 7241Baran, P. J. Am. Chem. Soc. 2011, 133, 801413
Ryan A Shenvi
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Corey:Synthesis of (-)-7-Methylomuralide
-J. Am. Chem. Soc. 2009, 131,5746–5747.14
Ryan A Shenvi
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Corey:Major pathways for diastereoselective tandem aldol/acyl-transferreactions
-J. Am. Chem. Soc. 2009, 131,5746–5747.15
Ryan A Shenvi
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Associate Professor of ChemistryUC Berkley
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-Baran, P. S.Nature 2007, 446, 404-408.
Total Synthesis Of Marine Natural Products Without Using Protecting Groups
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Thomas Maimone
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-Baran, P. S. J. Am. Chem. Soc. 2004,126, 7450–7451 -Baran, P. S.Nature 2007, 446, 404-408. 18
Thomas Maimone
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6 steps 7%yield 5 steps 13% yield
-Baran, P. S.Nature 2007, 446, 404-408. 19
Thomas Maimone
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Total Synthesis of Vinigrol
Vinigrol
-Angew. Chem. Int. Ed. 2008, 47, 3054-3056.-J. Am. Chem. Soc. 2009, 47, 17066-17067.
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Thomas Maimone
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Baran’s Approach: Retrosynthesis
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Thomas Maimone
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-J. Am. Chem. Soc. 2009, 47, 17066-17067. 23
Thomas Maimone
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23steps3% overall yield
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Thomas Maimone
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-J. Am. Chem. Soc. 2008, 130, 10886.-J. Am. Chem. Soc. 2009, 131, 6360. -J. Am.Chem. Soc. 2010, 132, 7119.
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-J. Am. Chem. Soc. 2008, 130, 10886
Larock indole synthesis
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Tim Newhouse
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IC50 = 5.4 µM, P388 murine leukemia cellsJ. Am. Chem. Soc. 2009, 131, 6360. J. Am.Chem. Soc. 2010, 132, 7119. 27
Tim Newhouse
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J. Am. Chem. Soc. 2009, 131, 6360. J. Am.Chem. Soc. 2010, 132, 7119. 28
Tim Newhouse
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J. Am.Chem. Soc. 2010, 132, 7119.29
Tim Newhouse
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Ryan A Shenvi Thomas Maimone Tim Newhouse
2010 Scripps 2012 UC Berkeley 2013 Yale
Now
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Shenvi’s Total Synthesis
-J. Am. Chem. Soc. 2013, 135, 1209−1212-J. Am. Chem. Soc. 2012, 134, 19604−19606
-Angew. Chem. Int. Ed. 2015, 54, 2410 –2415 -Nature Chem. 2015, 7, 604-607.
-J. Am. Chem. Soc. 2016, 138, 7268−7271
-J. Am. Chem. Soc. 2017, 139, 3647−3650-J. Am. Chem. Soc. 2017, 139, 9637−9644
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Ryan A Shenvi
DA大法好 DIMER MIHCHAEL ADDTION
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DA大法好
-J. Am. Chem. Soc. 2012, 134, 19604−19606 32
Ryan A Shenvi
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-J. Am. Chem. Soc. 2016, 138, 7268−7271
-J. Am. Chem. Soc. 2017, 139, 3647−3650
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Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines
-Nature 2013, 501, 195–199.34
Ryan A Shenvi
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DoubleMichael
-Nature Chem. 2015, 7, 604-607.-J. Am. Chem. Soc. 2017, 139, 3647−3650.
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Nature Chem. 2015, 7, 604-607. 36
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Nature Chem. 2015, 7, 604-607.37
Ryan A Shenvi
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-J. Am. Chem. Soc. 2017, 139, 3647−3650.38
Ryan A Shenvi
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-J. Am. Chem. Soc. 2013, 135, 1209−1212
Dimer
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Hydroarylation
J. Am. Chem. Soc. 2016, 138, 12779–12782.J. Am. Chem. Soc. 2016,138, 4962–4971.J. Am. Chem. Soc. 2018, 140, 16976−16981.J. Am. Chem. Soc. 2018, 140, 12056−12068.J. Am. Chem. Soc. 2018, 140, 11317−11324. 40
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-Angew. Chem. Int. Ed. 2014, 53, 3115-3119.
-J. Am. Chem. Soc. 2014, 136, 5287-5290.
-Angew. Chem. Int. Ed. 2015, 54, 1223-1226 -J. Am. Chem. Soc. 2015, 137, 10516−10519.
-Science. 2016, 352, 1078.-J. Am. Chem. Soc. 2016, 138, 14868−14871
-J. Am. Chem. Soc. 2016, 138, 16616−16619
-Angew. Chem. Int. Ed. 2017, 56, 1624 –1628
-J. Am. Chem. Soc. 2017, 139, 17783−17786 Maimone’s Total Synthesis41
Thomas Maimone
DA大法好 DIMER MIHCHAEL ADDTION TANDEM REACTION
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-Angew. Chem. Int. Ed. 2014, 53, 3115-3119. 42
Thomas Maimone
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-J. Am. Chem. Soc. 2014, 136, 5287-5290.43
Thomas Maimone
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-Angew. Chem. Int. Ed. 2015, 54, 1223-122644
Thomas Maimone
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-Angew. Chem. Int. Ed. 2015, 54, 1223-122645
Thomas Maimone
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J. Am. Chem. Soc. 2016, 138, 14868−14871
-Baran.P.S;Maimone.T.J. Nature 2007,445,826-827
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DA大法好 ADDTION TANDEM REACTION
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Peterson olefination
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