Biomimetic Synthesis and Structural Revision of (+/-)-Tridachiahydropyrone P. Sharma, N. Gri ﬃ ths, J. E. Moses, Org. Lett. 2008, 10, 4025 – 4027 Present.

Slides:

Advertisements

Similar presentations

Synthesis and Analysis of Aspirin Chemistry 1060 Laboratory.

Advertisements

211 PHC By: Dr. Reem Al-Wabli Dr. Ebtehal Al-Abdullah Dr. Maha Al-Mutairi.

We are grateful for the generous support from the National Science Foundation (CHE ). Introduction and History Attempted Cyclizations of Diphenyl.

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

Stereocontrolled Total Synthesis of (+)-Vinblastine Satoshi Yokoshima, Toshihiro Ueda, Satoshi Kobayashi, Ayato Sato, Takeshi Kuboyama, Hidetoshi Tokuyama,

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

Title Pericyclic Reactions Cycloaddition Electrocyclization.

Myers’ Synthesis of Dynemicin A. Andrew G. Myers 140 publications to date (1981) B.S. at MIT – undergraduate research with W. R. Roush. ( ) Graduate.

Chemistry 130 Chemical Equilibrium Dr. John F. C. Turner 409 Buehler Hall

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

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.

DEVELOPMENT OF A PHOTOCHROMIC NITROXYL DELIVERY SYSTEM David Spivey Mentor: Dr. Kevin P. Schultz Goucher College.

Synthesis of Chalcones: Starting Materials for the Synthesis Of Parasite-targeted Compounds Sarah Canché Lee Lab Group.

Cationic Olefin Polyannulations: History and Application to Steroid and Other Fused Polycycle Syntheses David A. Nicewicz.

Synthesis of Oil of Wintergreen

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

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 12 Alkenes, Alkynes, and Aromatic Compounds 12.2 Cis–Trans.

Tetrahydroisoquinoline: Oxidative imine formation, nucleophilic addition reactions and asymmetric selectivity James Fuster, Dr. Rina Soni, Professor Martin.

Supramolecular Laboratory Chulalongkorn University (THAILAND) Synthesis of Stilbene Crown Ether Calix[4]arenes and Their Isomerization 1 Abstract Five.

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

Carbon Chemistry: The Molecular Diversity of Life and The Structure and Function of Large Biological Molecules.

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.

Enantioselective Total Synthesis and Structure Revision of Spirodihydrobenzofuranlactam 1. Total Synthesis of Stachybotrylactam Org. Lett. 2003, 5, 1785.

Energy and Life Chapter 8 Biology Energy= the ability to do work Chemical Energy: stored in molecules and compounds (found in the food web) Light Energy:

Click chemistry for chitosan nanocarriers and biomaterials Ph.D. Student: Ingólfur Magnússon Instructor: Már Másson 7. June 2013 Research day.

CHE 311 Organic Chemistry I Dr. Jerome K. Williams, Ph.D. Saint Leo University.

Chapter 30 Orbitals and Organic Chemistry: Pericyclic Reaction Polar mechanism Radical mechanism Concerted process Electrocyclic reaction Cycloaddition.

Competitive Synthesis of Benzyl Naphthalenes David Waste Department of Chemistry, University of New Hampshire, Durham, NH December 5, 2013 Introduction:

MAPS. Dr. John Snow’s Cholera Map of London

Proteasome Inhibition by Fellutamide B Induces Nerve Growth Factor Synthesis John Hines, Michael Groll, Margaret Fahnestock, Craig M. Crews Chemistry &

Formal Ring-Opening/Cross-Coupling Reactions of 2-Pyrones: Iron-Catalysed Entry into Stereodefined Dienyl Carboxylates Dr. Chan-Liang Sun Pr. Alois FürstnerIron.

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

Alternatives to Bu 3 SnH in Radical Cyclisations: Copper Mediated 4-Exo and 5-Endo Radical Polar-Crossover Reactions Dr. Andrew Clark 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.

Chemical library in place Robust HT screen Hit Identification Chemical and biological validation Used to study biological processes Potential therapeutic.

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.

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

Total Syntheses of Di- and Tri-O-methyl Dynemicin A Methyl Esters Jack Taunton, John L. Wood, and Stuart L. Schreiber Department of Chemistry, Harvard.

Synthesis of New Scaffolds via Bisalkyne Cyclizations Catalyzed by Triflic Acid Jaime Alvarez Duque, Kyle Strom, John K. Snyder Boston University, Department.

Light and Palladium Induced Carbonylation Reactions of Alkyl Iodides Mechanism and Development Pusheng Wang Gong Group Meeting April 12 th 2014.

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.

A Synthesis of (+)-FR182877, Featuring Tandem Transannular Diels-Alder Reactions Inspired by a Postulated Biogenesis David A. Vosburg, Christopher D. Vanderwal,

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

Summary from Organic Chemistry Packet:. 1. Nomenclature based on alkanes Know alkanes for C 1 -C 10 Recognize the formula/name of – Alkenes (double bond)

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

Development of Photoremovable Protecting Groups. Photoremovable Protecting Groups and Cage Compounds The project develops new “cage compounds” for practical.

Progress towards the Synthesis of 1-Benzoxepin; A Model Oxepin Substrate Ian Smith, Ryan Fitzgerald, Holly Guevara, Arthur Greenberg

Forms of Energy Openers Mrs. V Science Match each definition to the correct key term A. B. C. D.

|| Welcome to the Library Connect Event Zurich Dr. Oliver Renn, Chemistry | Biology | Pharmacy Information Center, ETH Zurich Elsevier Library.

Phenols and Aryl Halides Nucleophilic Aromatic Substitution

2 Electrocyclic Reactions.

Conclusion and Future Work:

Zhengren Xu, Qian Wang, and Jieping Zhu*

Research projects for PhD/ Masters degree

Total Synthesis of (+)-Fastigiatine

Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4 + 3] Cycloaddition/SmI2‑Pinacol Coupling Ahmed H. E. Hassan,†,‡,§ Jae Kyun.

• First practical method for asymmetric hydrocyantion of a 1,3-diene

Because He Lives Studies in First John.

Concise Total Synthesis of (-)-Mersicarpine

crambescidin 800, crambescidin 359,

Use your Journal to Name the Transformations

Divergent Total Syntheses of (-)-Aspidospermine and (+)-Spegazzinine

Total Synthesis of Epothilone A: The Olefin Metathesis Approach

Synthesis and Properties of Alkene

IMPORTANT: Only a retrosynthesis is to be submitted for the first round molecule (NOT a forward synthesis). Please delete this text before submission.

Rationale Pathway Synthesis Expected Results Background

Presentation transcript:

Biomimetic Synthesis and Structural Revision of (+/-)-Tridachiahydropyrone P. Sharma, N. Gri ﬃ ths, J. E. Moses, Org. Lett. 2008, 10, 4025 – 4027 Present By Andrew Blemings

Dr. John E. Moses Master University of Bath, 2001, under Ian Rothwell PhD from University of Oxford, 2004, under Jack Baldwin Went to Scripps in 2004 Went to University of London in 2005 Appointed Associate Professor in 2007 Promoted to Reader of Chemical Biology in publications 1

Tridachiahydropyrones First isolated in 1996 by Cimino from mollusks Although synthesized by Jeffrey of Flinders in 2005, NMR did not match natural product Moses hoped to use Biomimetic chemistry to find the natural product Tridachiahydropyrones are used by mollusks to protect themselves from UV light Believed to occur via a 6 π electrocyclization from UV light –A thermal electrocyclization would produce the trans product –A light induced cyclization produces the cis product which matches the natural product 2

Woodward-Hoffman Rules #e-HeatLight 4nConDis 4n+2DisCon 3

Retrosynthesis 4

5

6

Forward Synthesis 7

Ran last step in MeOH, hv, for 60hrs –Isolated the cis isomer in 29% yield Ran the last step again in xylene at 150°C –Yielded no product 8

Questions 9