Assistant High School

Seth B. Herzon

Department of Chemistry

Yale University

*** ******** ******

New Haven, CT 06511

Phone: 203-***-****

E-mail: ****.******@****.***

Research Interests

Synthesis and study of complex natural products; mechanism of action and target identification studies of

anticancer and antimicrobial natural products; development of transformations and reagents of broad

utility for organic synthesis.

Academic Positions

7/2012 Present, Yale University

Associate Professor of Chemistry.

1/2011 Present, Yale University

Member, Yale Comprehensive Cancer Center.

6/2008 6/2012, Yale University

Assistant Professor of Chemistry.

8/2006 5/2008, University of Illinois

National Institutes of Health postdoctoral fellow with Professor John F. Hartwig. Projects

included the development and mechanistic study of transition metal-catalyzed C H bond

functionalization reactions and new strategies for reaction discovery.

8/2002 5/2006, Harvard University

Graduate student with Professor Andrew G. Myers. Developed convergent, enantioselective

syntheses of the complex alkaloids stephacidin B and avrainvillamide. Delineated the reactivity

of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide. Contributed towards target

identification and mechanism of action studies.

9/1999 7/2002, Temple University

Research assistant with Professor Grant R. Krow. Studied the preparation and reactivity of 2-

azabicyclo[2.1.1]hexanes. Synthesized conformationally constrained proline analogs based on

this core structure.

5/2001 8/2001, Merck Research Laboratories

Intern in the Department of Medicinal Chemistry. Synthesized non-peptidic HIV integrase

inhibitors.

Education

5/2006 Ph.D. in Chemistry, Harvard University

5/2002 B.S. in Chemistry, Temple University

5/1997 High School Diploma, Valley Forge Military Academy and College

Awards

2012 Camille Dreyfus Teacher Scholar Award

2012 Cottrell Scholar Award of the Research Corporation for Science Advancement

2012 Alfred P. Sloan Fellowship

2012 NSF CAREER Award

2011 Packard Fellowship in Science and Engineering

2011 Synthesis/Synlett Journal Award

2010 American Cancer Society Research Scholar Award

2010 Searle Scholar Award

2008 Eli Lilly New Faculty Award

2006 National Institutes of Health Postdoctoral Fellowship

2003 Harvard University Certificate of Distinction in Teaching

2003 National Science Foundation Graduate Research Fellowship

2002 The F. Albert Cotton and Al Tulinsky Prize

2002 Philadelphia Section of the American Chemical Society Award

2002 Richard Asher Paclin Memorial Prize

2002 Elected to Phi Beta Kappa

2002 Henry A. Sloviter Student Research Award in Chemistry (2nd Year)

2001 2002 Petroleum Research Fund Undergraduate Research Fellowship

2001 Henry A. Sloviter Student Research Award in Chemistry

Publications (Undergraduate, Graduate, Postdoctoral)

1. Hydroaminoalkylation of Unactivated Olefins with Dialkylamines. Seth B. Herzon and John F.

Hartwig J. Am. Chem. Soc. 2008, 130, 14940, DOI: 10.1021/ja806367e.

For commentary, see: (a) Ta(V)-Catalyzed Hydroaminoalkylation of Olefins with

Dialkyalmines. Paul Knochel and Andrei Gavryushin SYNFACTS 2009, 193, DOI:

10.1055/s-002*-*******. (b) Catalytic Hydroaminoalkylation. Peter W. Roesky

Angew. Chem., Int. Ed. Engl. 2009, 48, 4892, DOI: 10.1002/anie.200900735.

2. Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines. Seth

B. Herzon and John F. Hartwig J. Am. Chem. Soc. 2007, 129, 6690, DOI: 10.1021/ja0718366.

For commentary, see: Amine Synthesis Gains Utility. Stephen K. Ritter Chem. Eng.

News 2007, 85, 9.

3. Evidence for the Rapid Conversion of Stephacidin B into the Electrophilic Monomer

Avrainvillamide in Cell Culture. Jeremy E. Wulff, Seth B. Herzon, Romain Siegrist, and Andrew

G. Myers J. Am. Chem. Soc. 2007, 129, 4898, DOI: 10.1021/ja0690971.

4. Enantioselective Synthesis of Stephacidin B. Seth B. Herzon and Andrew G. Myers J. Am. Chem.

Soc. 2005, 127, 5342, DOI: 10.1021/ja0510616.

For commentary, see: Stephacidin B, the Avrainvillamide Dimer: A Formidable

Synthetic Challenge. Carmen Escolano Angew. Chem., Int. Ed. Engl. 2005, 44, 7670,

DOI: 10.1002/anie.200502383.

5. Identification of a Novel Michael Acceptor Group for the Reversible Addition of Oxygen- and

Sulfur-Based Nucleophiles. Synthesis and Reactivity of the 3-Alkylidene-3H-indole 1-Oxide

Function of Avrainvillamide. Andrew G. Myers and Seth B. Herzon J. Am. Chem. Soc. 2003,

125, 12080, DOI: 10.1021/ja0372006.

6. Convenient Preparations of 2,4-Methanopyrrolidine and 5-Carboxy-2,4-methanopyrrolidines.

Grant R. Krow, Guoliang Lin, Seth B. Herzon, Andrew M. Thomas, Keith P. Moore, Qiuli

Huang, and Patrick J. Carroll J. Org. Chem. 2003, 68, 7562, DOI: 10.1021/jo0348672.

7. The Rearrangement Route to 2-Azabicyclo[2.1.1]hexanes. Solvent and Electrophile Control of

Neighboring Group Participation. Grant R. Krow, Gouliang Lin, Deepa Rapolu, Yuhong Fang,

Walden S. Lester, Seth B. Herzon, and Philip E. Sonnet J. Org. Chem. 2003, 68, 5292, DOI:

10.1021/jo034394z.

8. Complex-Induced Proximity Effects. Temperature-Dependent Regiochemical Diversity in

Lithiation-Electrophilic Substitution Reactions of N-Boc-2-Azabicyclo[2.1.1]hexane. 2,4- and

3,5-Methanoprolines. Grant R. Krow, Seth B. Herzon, Gouliang Lin, Feng Qiu, and Philip E.

Sonnet Org. Lett. 2002, 4, 3151, DOI: 10.1021/ol026509b.

9. Synthesis of Novel 2-Azabicyclo[2.2.0]- and [2.1.1]hexanols. Grant R. Krow, Walden S. Lester,

Nian Liu, Jing Yuan, Amanda Hiller, Jinqi Duo, Seth B. Herzon, Yen Nguyen, and Kevin Cannon

J. Org. Chem. 2001, 66, 1811, DOI: 10.1021/jo001558s.

10. Azabicyclo[2.1.1]hexanes. 2. Substituent Effects on the Bromine-Mediated Rearrangement of 2-

Azabicyclo[2.2.0]hex-5-enes. Grant R. Krow, Yoon B. Lee, Walden S. Lester, Nian Liu, Jing

Yuan, Jinqi Duo, Seth B. Herzon, Yen Nguyen, and David Zacharias J. Org. Chem. 2001, 66,

1805, DOI: 10.1021/jo0015570.

Publications (Yale University)

1. Regioselective Reductive Hydration of Alkynes to Form Branched or Linear Alcohols. Le Li and

Seth B. Herzon J. Am. Chem. Soc. 2012, 134, in press.

2. Synthesis of (R)- -4-Methyl-cyclohex-2-ene-1-one. Maung Kyaw Moe Tun and Seth B. Herzon

J. Org. Chem. 2012, 77, Article ASAP, DOI: 10.1021/jo3017956.

3. Development of Enantioselective Synthetic Routes to -Kinamycin F and -Lomaiviticin

Aglycon. Christina M. Woo, Shivajirao L. Gholap, Liang Lu, Miho Kaneko, Zhenwu Li, P.C.

Ravikumar, and Seth B. Herzon J. Am. Chem. Soc. 2012, 134, Article ASAP, DOI:

10.1021/ja307497h.

4. Isolation of Lomaiviticins C E. Transformation of Lomaiviticin C to Lomaiviticin A, Complete

Structure Elucidation of Lomaiviticin A, and Structure Activity Analyses. Christina M. Woo,

Nina E. Beizer, Jeffrey E. Janso, and Seth. B. Herzon J. Am. Chem. Soc. 2012, 134, 15285, DOI:

10.1021/ja3074984.

For commentary, see: A Lomaiviticin is Scarce No More. Stuart Borman Chem. Eng.

News 2012, 90, 9.

5. The Pharmacology and Therapeutic Potential of -Huperzine A. Maung Kway Moe Tun, and

Seth B. Herzon J. Exp. Pharmacol. 2012, 4, 113, DOI: 10.2147/JEP.S27084.

6. Room Temperature, Palladium-Mediated P Arylation of Secondary Phosphine Oxides. Aaron J.

Bloomfield, and Seth B. Herzon Org. Lett. 2012, 14, 4370, DOI: 10.1021/ol301831k

7. Real Time Kinetics of Surfactant Molecules Transfer Between Emulsion Particles Probed by In

Situ Second Harmonic Generation Spectroscopy. YuMeng You, Aaron J. Bloomfield, Jian Liu, Li

Fu, Seth B. Herzon, and Elsa C. Y. Yan J. Am. Chem. Soc. 2012, 134, 4264 DOI:

10.1021/ja2104608.

8. Characterization of a Reductively-Activated Elimination Pathway Relevant to the Biological

Chemistry of the Kinamycins and Lomaiviticins. Seann P. Mulcahy, Christina M. Woo, Weidong

Ding, George A. Ellestad, and Seth B. Herzon Chem. Sci. 2012, 3, 1070, DOI:

10.1039/C2SC00854H.

9. The Diazofluorene Antitumor Antibiotics: Structural Elucidation, Biosynthetic, Synthetic, and

Chemical Biological Studies. Seth B. Herzon and Christina M. Woo Nat. Prod. Rep. 2012, 29,

87, DOI: 10.1039/C1NP00052G.

10. Enantioselective Syntheses of -Kinamycin F and -Lomaiviticin Aglycon. Seth B. Herzon

Synlett 2011, 2105, DOI: 10.1055/s-003*-*******

11. A Robust and Scalable Synthesis of the Potent Neuroprotective Agent -Huperzine A. Maung

Kway Moe Tun, Daniel-Joachim W stmann, and Seth B. Herzon Chem. Sci. 2011, 2, 2251,

DOI:10.1039/C1SC00455G.

For commentary, see: (a) Rapid Route to Huperzine A. David Barden Chem. World 2011. (b)

Synthesis of -Huperzine A. Steven V. Ley and Philippa B. Cranwell SYNFACTS 2011, 7,

DOI: 10.1055/s-003*-*******.

12. Efficient Entry to the Hasubanan Alkaloids. First Enantioselective Total Syntheses of -

Hasubanonine, -Runanine, -Delavayine, and -Periglaucine B. Seth B. Herzon, Nicholas

A. Calandra, and Sandra M. King Angew. Chem., Int. Ed. Engl. 2011, 50, 8863, DOI:

10.1002/anie.201102226.

Featured on the cover of issue 38 of Angewandte.

Selected by the editors as a Hot Paper .

13. 11-Step Enantioselective Synthesis of -Lomaiviticin Aglycon. Seth B. Herzon, Liang Lu,

Christina M. Woo, and Shivajirao L. Gholap J. Am. Chem. Soc. 2011, 133, 7260, DOI:

10.1021/ja200034b.

For commentary, see: (a) Linking Lomaiviticin. Carmen Drahl Chem. Eng. News 2011,

86, 8. (b) Happy Couple. Jake Yeston Science 2011, 331, 823, DOI:

10.1126/science.331.6019.823-d. (c) 11-Step Enantioselective Synthesis of -

Lomaiviticin Aglycon. Matteo Zanda Synform 2011, A70.

Featured on the cover of issue 18 of J. Am. Chem. Soc.

14. Single-Step Synthesis of Secondary Phosphine Oxides. Aaron J. Bloomfield, Jack M. Qian*, and

Seth B. Herzon Organometallics 2010, 29, 4193, DOI: 10.1021/om100571w.

15. Development of a Convergent Entry to the Diazofluorene Antitumor Antibiotics:

Enantioselective Synthesis of Kinamycin F. Christina M. Woo, Liang Lu, Shivajirao L. Gholap,

Devin R. Smith*, and Seth B. Herzon J. Am. Chem. Soc. 2010, 132, 2540, DOI:

10.1021/ja910769j.

For commentary, see: Expedient Total Synthesis of Kinamycin F. Mark Lautens and

David A. Candito SYNFACTS 2010, 552, DOI: 10.1055/s-002*-*******.

16. Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A. Shivajirao L.

Gholap, Christina M. Woo, P. C. Ravikumar, and Seth B. Herzon Org. Lett. 2009, 11, 4322, DOI:

10.1021/ol901710b.

Book Chapters

1. John F. Hartwig and Seth B. Herzon Amido Complexes of the Early Transition Metals.

Organotransition Metal Chemistry, 1st Ed., University Science Books: Sausalito, California,

2010, p. 152.

Professional Consulting

Scientific Consultant, Satori Pharmaceuticals, Cambridge MA (2008 present)

Member, Scientific Advisory Board, JustBIO, Qu bec, Canada (2008 present)

Scientific Consultant, Biomedisyn Incorporated, Woodbridge, CT (2011)

Member, Scientific Advisory Board, Insero Health, Inc., Miami, FL (2012 present)

Personal

Born July 26th, 1979, Philadelphia, PA.

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