Michael J. Krische B.S.in Chemistry from University of California at Berkeley (1989) Fulbright Fellow at Helsinki University (1990) Ph.D. in Chemistry.

Slides:

Advertisements

Similar presentations

Prepared by : Malak Eshtayah

Advertisements

Total Synthesis of Prostaglandins F 2α and E 2 as the naturally occurring forms Kirk W. Shimkin Total Synthesis Spring 2012 Corey, et al. JACS, 1970, 92,

Synthesis of Vancomycin from the Aglycon Christopher Thompson, Min Ge, Daniel Kahne J. Am. Chem. Soc. 1999, 121, Presented by James Melnyk.

Total Synthesis of (±)-Longifolene Yiyun Peng March 4th, 2013 W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583 – 2584.

Department of Chemistry Seminar Announcement Date/Time/VenueTitle/Speaker 25 Jan (Tue) 11am – S8 Level 3 Executive Classroom Rh-Catalyzed [(5+2)+1],

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

1 D. A. Evans’ Asymmetric Synthesis — From 80’s Chiral Auxiliary to 90’s Copper Complexes and Their Applications in Total Synthesis Supervisor: Professor.

Catalytic Cross-coupling Reactions with Unactivated Alkyl Electrophiles and Alkyl Nucleophiles Heng Su 04/11/2008 Department of Chemistry Brandeis University.

Total Synthesis and Evaluation of [ψ[CH 2 NH]Tpg 4 ] Vancomycin Aglycon: Reengineering Vancomycin for Dual D -Ala- D - Ala and D -Ala- D -Lac Binding Brendan.

Recent Development for Stereoselective Synthesis of 1,3-Polyol Ye Zhu Prof. Burgess’ Group Aug. 19, 2010.

Enantioselective Total Synthesis of Ecteinascidin 743

Alkylation by Asymmetric Phase- Transfer Catalysis 张文全.

First Total Synthesis of (±)-Strychnine via a [4+2]- Cycloaddition/Rearrangement Cascade Hongjun Zhang, Jutatip Boonsombat, and Albert Padwa* Org. Lett.

Department of Chemistry Seminar Announcement Date/Time/VenueTitle/Speaker 21 Feb (Mon) 4pm – S8 Level 3 Executive Classroom Natural products and.

Silas P. Cook Education: B.A. Reed College (1999);

Olefin Metathesis and Use in Tandem Reactions - The Work of Marc L. Snapper James Mousseau Literature Meeting 6 May

化学系 Department of Chemistry Catellani Reaction

The Career of Chao-Jun Li Guochang B.S. Zhengzhou University 1979 M.S. Chinese Academy of Science 1985 Tak-Hang ChanTak-Hang Chan Ph.D. McGill.

Career-in-review Keiji Maruoka Reporter: Li Chen Supervisor: Prof. David Zhigang Wang

Lecture 33 Rotational spectroscopy: energies (c) So Hirata, Department of Chemistry, University of Illinois at Urbana-Champaign. This material has been.

Cations Carey & Sundberg, Part A Chapter 5, "Nucleophilic Substitution",

Microwave- Assisted Synthesis of 1,3- Dimesitylimidazolinium Chloride Brittney Hutchinson Department of Chemistry, University of New Hampshire, Durham,

International Workshop on Nuclear Dynamics and Thermodynamics Honoring the achievements of Joseph B. Natowitz Robert E. Tribble Texas A&M University August.

Enantioselective Total Syntheses of Manzamine A and Related Alkaloids John M. Humphrey, Yusheng Liao, Amjad Ali, Tobias Rein, Yue-Ling Wong, Hui-Ju Chen,

Buchwald-Hartwig Cross Coupling Reaction Reporter: Ying-Chieh CHAO Lecturer: Professor Guey-Sheng Liou Advisor: Professor Ru-Jong Jeng Data:2013/12/27.

Total Synthesis of (+)-Discodermolide CHEM635 Kelsey Roberts Group B February 19, 2013 Patterson, I*; Florence, G. J.; Gerlach, K.; Scott, J. P. Agnew.

Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins Via an Ene Reaction / [2,3]-Rearrangement Hongli Bao & Uttam K. Tambar Guillaume.

Total synthesis of 6-Deoxyerethronolide B CHEM 635 Kelsey Roberts 05/07/13 Gao, X.; Woo, S.K.; Krische M.J. J. Am. Chem. Soc. 2013, 135, 4223.

Department of Chemistry Seminar Announcement Date/Time/VenueTitle/Speaker 14 Mar (Mon) 11am – S8 Level 3 Executive Classroom Structure and Dynamics.

Synthesis and Biological Activity of Platensimycin

Song jin July 10, 2010 Gong Group Meeting.

Total Synthesis of the Antimitotic Bicyclic Peptide Celogentin C

Peptidomimetics and Mimicry of  -Strand / Sheets and  -Sheet Sandwiches Jian Liu Merck & Co., Inc. Rahway, NJ

Utilization of Ring Closing Metathesis in Alkaloid Synthesis I. Synthetic Studies on the Immunosuppressant FR II. Toward the Total Synthesis of Lundurines.

Created by Professor William Tam & Dr. Phillis Chang Ch Chapter 18 Reactions at the  Carbon of Carbonyl Compounds Enols and Enolates.

Kenneth T. Whitby Award American Association for Aerosol Research.

Asymmetric BINOL-Phosphate Derived Brønsted Acids: Development and Catalytic Mechanism Reporter: Song Feifei Supervisor: Prof. Yong Huang

Rhodium-Catalyzed Chemo- and Regioselective Decarboxylative Addition of β- Ketoacids to Allenes: Efficient Construction of Tertiary and Quaternary Carbons.

Synthesis of Leucascandrolide A via a Spontaneous Macrolactolization J. Am. Chem. Soc. 2002, 124, Presented by Vijayarajan Devannah 3/19/2013.

The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation J.A. Enquist, Jr., B.M. Stoltz, Nature 2008,453,1228.

Regioselective reactions of 3,4-pyridynes enabled

Asymmetric Total Synthesis of Caribenol A Author: Zhen Yang J. Am. Chem. Soc. 2010, 132, Presented by Daniel Roberts April 6 th 2014.

The Work Of Pr Karl A. Scheidt Group Department of Chemistry, Northwestern UniVersity, Evanston.

Redox Neutral Reactions Wang Chao Redox Economy and Redox Neutral Reactions: Angew. Chem. Int. Ed. 2009, 48, 2854 – 2867.

Erik J. Sorensen B.A. in Chemistry from Syracuse University (1989)

Peter Yates ( ) B.Sc from the University of London, 1946.

Synthesis of Discodermolides Useful for Investigating Microtubule Binding and Stabilization Melissa G. Morris CHEM 635 February 12, 2013 Hung, D. T.; Nerenberg,

Synthesis of novel polycyclic aromatic hydrocarbons by transannular cyclization Tobe Laboratory M1 Yamane Hiroshi.

3D model of Vindoline.

Rychnovsky’s Formal Synthesis of Leucascandrolide A Presented by BriAnne Bentivegna March 19, 2013 University of Delaware Kopecky, D.J.; Rychnovsky, S.D.

C-H Insertion Story Justin Du Bois associate professor : University of Stanford B.S. : University of California at Berkeley (1992) Ph.D. : California Institute.

Enantioselective Reactions Catalyzed by Iron Complexes Pablo Pérez.

Selected examples of Domino Reactions in Total Synthesis Dagoneau Dylan Zhu Group Frontiers in Chemical Synthesis May 22 th, 2014.

学术报告报告名称： Functional Inorganic Materials: Molecular Recognition, Chiral Separation and Water Oxidation 报告人：Prof.Samar Kumar Das 时间：（周二）

Phenols and Aryl Halides Nucleophilic Aromatic Substitution

Zhengren Xu, Qian Wang, and Jieping Zhu*

BIOGENETICALLY INSPIRED TOTAL SYNTHESIS OF LYCOPODIUM ALKALOIDS,(+)-FLABELLIDINE AND (–)-LYCODINE Masayuki Azuma, Tetsuya Yoshikawa, Noriyuki Kogure, Mariko.

Reaction mechanism of the Michael addition reaction between a nucleophile and a polarized double bond. Source: Nucleophilic Substitution, Addition, and.

学堂讲座通知化学系 Prof. Liming Zhang 加州大学Santa Barbara分校

HONORS AND AWARDS 时间： :30 地点：礼东二楼报告厅 TITLE

Academic Lecture Rational Synthesis and Assembly of Nanocatalysts for Energy Applications 报告人：Prof. Shouheng Sun (Brown University,美国布朗大学) 时间：

Total Synthesis of Leucascandrolide A

Michael J. Krische Presented by Louis-Philippe Beaulieu

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes

Kiyoun Lee and Dale L. Boger*

Total Synthesis of Epothilone A: The Olefin Metathesis Approach

Angew. Chem. Int. Ed., 2010, 49, Early View

DIVERGENT TOTAL SYNTHESES OF LYCONADINS A AND C

Principles of Organic Synthesis in Pure Water

Professor Vy Dong Department of Chemistry, University of California at Irvine Born in Big Spring, Texas, first in her Vietnamese family to attend college.

Presentation transcript:

Krische’s Total Synthesis of Cyanolide A Presented by BriAnne Bentivegna May 7, 2013 University of Delaware Waldeck, A.R.; Kriche, M.J. Angew. Chem. Int. Ed. 2013, 52, 4470

Michael J. Krische B.S.in Chemistry from University of California at Berkeley (1989) Fulbright Fellow at Helsinki University (1990) Ph.D. in Chemistry from Stanford University (1990-1996) NIH Post-Doc at Université Louis Pasteur (1997-1999) Individual Career at the University of Texas at Austin Assistant Professor of Chemistry (1999-2003) Professor of Chemistry (2004-Present) Robert A. Welch Chair in Science (2007-Present) Awards include ACS Cope Scholar Award, ACS Elias J. Corey Award, National Science Foundation Career Award, Camille Dreyfus Teacher-Scholar Award and many more. 175 publications to date 160 publications from his independent career

Cyanolide A Isolated from the Papua New Guinea cyanobacterium Lyungbya bouillonii Exhibits potent molluscicidal activity against Biomphalaria glabrata, a water snail This water snail is a vector of the human parasitic disease schistosomiasis which ranks second behind malaria among human parasitic diseases There are drugs that exist to treat those who are infected but reducing or eliminating the population of these infected water snails is more desirable Hence, efforts to synthesize Cyanolide A have been put forth by many chemists as an alternate molluscididal agent A total of 6 chemists excluding Krische have synthesized Cynaolide A ranging from 18 to 22 total steps

Retrosynthesis

Beginning Steps

Ending Steps Cyanolide A!!!

2nd Generation Synthesis Cyanolide A!!!

Conclusion Cyanolide A was synthesized in 7 linear/11 total steps and 6 linear/10 total steps NO Protecting Groups, Chiral Auxiliaries or Premetalated Carbon Nucleophiles were used!!! Questions?

Double Allylation Mechanism Kim, I.S.; Han, S.B.; Kische, M.J. J. Am. Chem. Soc. 2009, 131, 2514

Oxa-Michael Cyclization Mechanism Fuwa, H.; Noguchi, T.; Noto, K. Sasaki, M. Org. Biomol. Chem. 2012, 10, 8108