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Chen Peihao 2019-4-21

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

Isolation of Chartelline alkaloids

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Ryan A Shenvi

Biosynthesis

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Ryan A Shenvi

-JACS, 2006, 128,14028-14029.

–Angew. Chem. Int. Ed. 2005, 44, 3714–3717.8

Ryan A Shenvi

Model Study

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Overall yield 0.072% 9

Ryan A Shenvi

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

Baran: A-Ring Functionalization

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Ryan A Shenvi

Baran: B-Ring Expansion

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Ryan A Shenvi

Baran: Isoquinoline Installation

Baran, P. J. Am. Chem. Soc. 2008, 130, 7241Baran, P. J. Am. Chem. Soc. 2011, 133, 801413

Ryan A Shenvi

Corey：Synthesis of (-)-7-Methylomuralide

-J. Am. Chem. Soc. 2009, 131,5746–5747.14

Ryan A Shenvi

Corey：Major pathways for diastereoselective tandem aldol/acyl-transferreactions

-J. Am. Chem. Soc. 2009, 131,5746–5747.15

Ryan A Shenvi

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

-Baran, P. S. J. Am. Chem. Soc. 2004,126, 7450–7451 -Baran, P. S.Nature 2007, 446, 404-408. 18

Thomas Maimone

6 steps 7%yield 5 steps 13% yield

-Baran, P. S.Nature 2007, 446, 404-408. 19

Thomas Maimone

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

Baran’s Approach: Retrosynthesis

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Thomas Maimone

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Thomas Maimone

-J. Am. Chem. Soc. 2009, 47, 17066-17067. 23

Thomas Maimone

23steps3% overall yield

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Thomas Maimone

-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

IC50 = 5.4 µM, P388 murine leukemia cellsJ. Am. Chem. Soc. 2009, 131, 6360. J. Am.Chem. Soc. 2010, 132, 7119. 27

Tim Newhouse

J. Am. Chem. Soc. 2009, 131, 6360. J. Am.Chem. Soc. 2010, 132, 7119. 28

Tim Newhouse

J. Am.Chem. Soc. 2010, 132, 7119.29

Tim Newhouse

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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DA大法好 DIMER MIHCHAEL ADDTION

DA大法好

-J. Am. Chem. Soc. 2012, 134, 19604−19606 32

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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

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

Ryan A Shenvi

Nature Chem. 2015, 7, 604-607.37

Ryan A Shenvi

-J. Am. Chem. Soc. 2017, 139, 3647−3650.38

Ryan A Shenvi

-J. Am. Chem. Soc. 2013, 135, 1209−1212

Dimer

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Ryan A Shenvi

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

Ryan A Shenvi

-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

-Angew. Chem. Int. Ed. 2014, 53, 3115-3119. 42

Thomas Maimone

-J. Am. Chem. Soc. 2014, 136, 5287-5290.43

Thomas Maimone

-Angew. Chem. Int. Ed. 2015, 54, 1223-122644

Thomas Maimone

-Angew. Chem. Int. Ed. 2015, 54, 1223-122645

Thomas Maimone

J. Am. Chem. Soc. 2016, 138, 14868−14871

-Baran.P.S;Maimone.T.J. Nature 2007,445,826-827

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-Science. 2016, 352, 1078.48

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-Angew. Chem. Int. Ed. 2017, 56, 1624 –162850

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-Angew. Chem. Int. Ed. 2017, 56, 1624 –162851

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-Tenaglia,A.; Terranova, E.; Waegell, B. J. Org. Chem. 1992, 57, 5523.54

Thomas Maimone

-J. Am. Chem. Soc. 2017, 139, 631−634 -J. Am. Chem. Soc. 2017, 139, 1790−1793 -J. Am. Chem. Soc. 2018, 140, 2062−2066

-J. Am. Chem. Soc. 2019, 141, 1479−1483

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Tim Newhouse

DA大法好 ADDTION TANDEM REACTION

-J. Am. Chem. Soc. 2015, 137, 5875. 56

Tim Newhouse

-J. Am. Chem. Soc. 2015, 137, 5875.

-J. Am. Chem. Soc. 2016, 138, 1166.

-Angew.Chem. Int. Ed. 2017, 56, 8258.

-Angew. Chem. Int. Ed. 2017, 56, 13132.

-J. Am. Chem. Soc. 2019, Articles ASAP 57

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-J. Am. Chem. Soc. 2017, 139, 631−634 58

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-J. Am. Chem. Soc. 2018, 140, 2062−2066 60

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-J. Am. Chem. Soc. 2018, 140, 2062−2066 61

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-J. Am. Chem. Soc. 2017, 139, 1790−1793 63

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-J. Am. Chem. Soc. 2017, 139, 1790−1793 64

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Peterson olefination

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