Synthesis of Leucascandrolide A via a Spontaneous Macrolactolization J. Am. Chem. Soc. 2002, 124, 13670-13671 Presented by Vijayarajan Devannah 3/19/2013.

Slides:

Advertisements

Similar presentations

CAREER: Gold Nanoparticles with Single Surface Functional Groups: Synthesis and Study PI: Qun Huo, North Dakota State University, DMR Objective:

Advertisements

Total Synthesis of (+)-Saxitoxin

Amphidinolide A Isolation: 1. Kobayashi, J. et al. Tetrahedron Lett. 1986, 27, Kobayashi, J. et al. J. Nat. Prod. 1991, 54, Biological Activity:

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

Amos B. Smith Mounuo Cheng Prof. Amos B. Smith Rhodes-Thompson Professor of Chemistry University of Pennsylvania, Amos B. Smith, III (born August.

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.

Amphidynamic Crystalline Materials Based on Inertial Rotors and Dipolar Arrays Miguel A. Garcia-Garibay, University of California-Los Angeles, DMR

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

Molecular things you want Molecular things you have ? chemists.

Lactacystin: An Inhibitor in the Ubiquitin Proteasome Pathway Ami Jun-Yee Chin February 17, 2005.

1 Li Xiao and Lichang Wang Department of Chemistry & Biochemistry Southern Illinois University Carbondale The Structure Effect of Pt Clusters on the Vibrational.

.  Based on particle size and surface charge characterization studies, both nanoparticles have successfully been synthesized.  Successful conjugation.

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

Ali A. El-Gamal, Shang-Kwei Wang and Chang-Yih Duh Department of Marine Biotechnology and Resources, National Sun Yat-sen University; Kaohsiung, Taiwan.

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.

Welwitindolinones Tiffany Piou Group meeting

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.

Enolate Heterocoupling: A Different Kind of Direct Functionalization A Phil S. Baran Methodology 27 October 2009 A Phil S. Baran Methodology 27 October.

Catalytic Asymmetric Total Syntheses of Quinine and Quinidine Izzat T. Raheem, Steven N. Goodman, and Eric N. Jacobsen J. Am. Chem. Soc. 2004, 126, 3,

Kang Hyun Jung. Introduction Leucascandrolide A (1, Scheme 1) was isolated in 1996 from the calcareous sponge Leucascandra caveolata, collected off the.

A Cycloaddition Cascade Approach to the Total Synthesis of (-)-FR David A. Evans and JeremyT.Starr Presented by Vijayarajan Devannah 2/19/2013.

Synthesis and Characterization of Amphiphilic Dendron Coils – Potential Nanomicelle Precursors Jeromy T. Bentley, RET Fellow 2011 Naperville Central High.

Elucidation of the intra-chain radical mechanism in poly(norbornene imide) single-chain nanoparticle formation Justin P. Cole, Jacob J. Lessard, Christopher.

Single-Chain Nanoparticles from Sequenced Polyolefins Acknowledgments Thank you to Dr. Erik Berda and the Berda research group for allowing me to join.

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

UIC College of Engineering Six Academic Departments with Graduate and Undergraduate Programs Bioengineering, Chemical Engineering, Civil & Materials Engineering,

Efficient Entry to the Hasubanan Alkaloids: First Enantioselective Total Synthesis of (-)- Hasubanonine, (-)-Runanine, (-)-Delavayine, and (+)-Periglaucine.

1 Department of Electrical and Computer Engineering at and its Center of Rail Safety-Critical Excellence Ted Giras, Professor Zongli Lin, Associate Professor.

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.

Synthesis of Garner’s Aldehyde Carmen Cannon, Kristina Truitt, Rachel Andrews, Bette’ Ford and Victoria Geisler Department of Chemistry, University of.

A New Stereocontrolled Total Synthesis of the Mast Cell Inhibitory Alkaloid (+)-Monanchorin KarlJ.Hale* and Liping Wang. Org. Lett., 2014, 16 (7), xxxx.

Tandem Catalytic Polymerization as Efficient Method to Synthesize Organic Nanoparticles Zhibin Guan, University of California - Irvine DMR Highly.

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,

3D model of Vindoline.

John Robert Schrieffer By: Tyler Schuttloffel. His Life He was born in Oak Park Illinois. Born on May 31, Graduated in Eustis High School in 1949.

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

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

Access to the Akuammiline Family of Alkaloids : Total Synthesis of (+)-Scholarisine A Speaker ： Yi-Chih Lu Date ： 2013/4/20 Gregory L. Adams, Patrick J.

Concise Total Synthesis of (+)-Lyconadin A Speaker: Chia-Fu Chang J. Am. Chem. Soc. Takuya Nishimura, Aditya K. Unni, Satoshi Yokoshima, Tohru Fukuyama*

Total Synthesis of (—)-Acetylaranotin Hideto Fujiwara, Taichi Kurogi, Shun Okaya, Kentaro Okano, and Hidetoshi Tokuyama* Angew. Chem. Int. Ed. 2012, 51,

Total Synthesis of Manzamine A and Related Alkaloids

SYNTHESIS OF CHOLANE AND LANOSTANE DERIVATIVES

Sean Pierre-Louis, Marc Boudreau, Bill Butler

Partial Synthesis of Heliotridane

Total Synthesis of the Potent cAMP Signaling Agonist (–)-Alotaketal A

Synthesis of Super Potent Antibiotic Cystobactamide 861-2

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

美国伊利诺大学香槟分校Jianjun Cheng报告

Goldwater Scholar Katie Peterson (Klotz), 2008 Where is she now?

Total Synthesis of Leucascandrolide A

Jennifer Chouinard, Prof. Erik Berda

crambescidin 800, crambescidin 359,

The First Conventional Synthesis of 1-methyl-4-silatranone and

Total Synthesis of Epothilone A: The Olefin Metathesis Approach

DIVERGENT TOTAL SYNTHESES OF LYCONADINS A AND C

Synthesis of p-xylene diisocyanide and Polymerization

Olesya A. Ulanovskaya, Jiayue Cui, Stephen J. Kron, Sergey A. Kozmin

Interleukin 15 is a potent stimulant of intraepithelial lymphocytes

Joey Mancinelli, Justin Cole, Erik Berda

Joey Mancinelli, Justin Cole, Erik Berda

D7 Taxol Essential idea Chiral auxiliaries allow the production of individual enantiomers of chiral molecules.

Synthesis of Functionalized BODIPY Dyes for Use as Fluorescent Probes

Presentation transcript:

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

About Professor Sergey A. Kozmin Education and Professional Undergraduate Research Assistant with Professor Irina P. Beletskaya Lomonosov Moscow State University, Moscow, Russia Graduate Research Assistant with Professor Viresh H. RawalUniversity of Chicago, Chicago, Illinois Postdoctoral Associate with Professor Amos B. Smith, III University of Pennsylvania, Philadelphia, Pennsylvania Assistant Professor, University of Chicago Associate Professor, University of Chicago 2011-present Professor, University of Chicago Notable Awards 2003 Alfred P. Sloan Fellow 2004 American Cancer Society Research Scholar 2004 Amgen Young Investigator’s Award 2004 Camille Dreyfus Teacher-Scholar Award 2005 NSF CAREER Award 2005 GlaxoSmithKline Chemistry Research Scholar 1

About Leucascandrolide A Its is a highly bioactive marine macrolide isolated from new genus of calcerous sponges Leucascandra caveolata. It displays potent cytotoxicity against KB and P388 tumor cell lines ( IC ng/ml and 0.25 μg/mL respectively), and it also a strong inhibitor of animal-pathogenic yeast candida albicans. Structural Features of Leucascandrolide A It possess a 14 membered lactone It includes dioxotricyclic core It is highly unsaturated and contains oxazole in its side chain. 2

Retrosynthesis 3

Synthesis of C 1 -C 15 Fragment 4 Scheme 2 Scheme 3

Continues…… 5 Scheme 4 Scheme 5

Formation of crucial Macrocycle 6 Scheme 5

Synthesis of Oxazole side chain and completion of the target Leucascandrolide A 7 Scheme 6

Conclusion Racemic Leucascandrolide A was synthesized in longest linear sequence of 18 steps from commercially available precursors. 500 MHz 1 H NMR and 125 MHz 13 C NMR spectra of synthetic Leucascandrolide A was in excellent agreement with those reported in literature. Total yield is 2% 8

Thank You 9