Synthesis of Biyouyanagin A

Slides:

Advertisements

Similar presentations

Lab A: Vincent Lindsay, Cyril Nicolas, Pascal Cérat and Sébastien Goudreau Synthesis Meeting Proposed Total Synthesis of Haliclonin A November 7 th, 2009.

Advertisements

Chlorophyll biosynthesis. In the first phase of chlorophyll biosynthesis: The amino acid glutamic acid is converted to 5- aminolevulinic acid (ALA). This.

Conjugated Dienes and U.V. Spectroscopy. Some Dienes.

Organometallic Compounds Chapter 15. Carbon Nucleophiles: Critical in making larger organic molecules. Review some of the ones that we have talked about….

Heterocyclic Chemistry

Friedel–Crafts Acylation Reactions The electrophile is an acylium ion.

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.

Low valent of Vanadium catalyst in organic synthesis.

Biological Synthesis of “Fatty” Acids. Enzyme = ‘fatty acid synthase” (multifunctional enzyme) Condensing Enzyme (CE) Acyl Carrier Protein (ACP)

Heterocyclic Chemistry

Second Semester Organic Chemistry Options: Bioorganic or Organic Mechanism and Synthesis Albert Matlin and Jason Belitsky Department of Chemistry and Biochemistry.

Alkylation of Aldehydes and Ketones 18-4 Alkylation of enolates can be difficult to control. The alkylation of an aldehyde or ketone enolate is an example.

1 Aromatic Compounds  Aromatic compounds contain benzene.  Benzene C 6 H 6 has 6 C atoms and 6 H Atoms  Two possible ring structures show benzene.

1 Single electron transfer reaction involving 1,3-dicarbonyl compounds and its synthetic applications Reporter: Jie Yu Oct. 31, 2009.

Alkenes:Formation by elimination reactions (McM 11.12, 11.13) Substitution reactions:Cleavage of ethers (McM 18.5) Organometallic coupling react. (McM.

Reactions Catalyzed by Rhenium Carbonyl Complexes 杜宇鎏

Limitations on Friedel-Crafts Alkylation

Litterature Meeting Enantioselective Total Synthesis of Avrainvillamide and Stephacidins A and B Aspergillus ochraceus.

Amines Nomenclature Properties Preparation reactions

Organometallic Compounds

Mingli Li ( stored as THF solutions, blue-green for SmI 2 and yellow-green for YbI 2 ) Deoxygenation Reactions Reductions of Double Bonds.

Total synthesis of Piperazic acid-containing natural products: Piperazimycin A and Chloptosin Liu Bin

1 The objectives of the 4 th Handout are to know about: PHCM 331 – Organic and Medicinal/Pharmaceutical Chemistry I Handout # 4 Winter 2015 / 2016 Some.

1 Chapter 7 Ring closure (and ring opening) 7.1Intramolecular cyclization by electrophile- nucleophile 7.2Cycloadditon 7.3Electrocyclic ring closure 7.4Ring.

Enantioselective Reactions Catalyzed by Iron Complexes Pablo Pérez.

Tandem carbonylation reaction. Monsanto Process (Acetic acid Synthesis): o c, 1-40 atm Ref: BASF process: cobalt-based high pressure process.

Chemical Biology What’s Chemical biology? Why should we learn?

Synthesis of Daphnilongeranine C

Friedel–Crafts reaction

Zhengren Xu, Qian Wang, and Jieping Zhu*

Synthesis of Heterocyclic Rings 2 (Cyclization at double bonds)

Heterocyclic Chemistry

Heterocyclic Chemistry

Chapter 10 Organohalides

Total Synthesis of (+)-Fastigiatine

Chapter 15: Alcohols, Diols, and Ethers

3 Cycloaddition and Cycloreversion Reactions.

Total Synthesis of (±)-Cylindricine C

Carbon-Carbon Bond Formation and Synthesis

Friedel–Crafts reaction

Chapter 10 Organohalides

Chemistry 2100 Chapter 17.

C-H Insertion on sulfonyl compounds Synthesis of Plakortethers

Heterocyclic Chemistry

Literature Meeting February 20th 2006

Alkene Reactions Addition Substitution Diels-Alder Cleavage.

Alkyne Reactions Addition Substitution Diels-Alder Cleavage.

Ch. 10 – Conjugation in Alkadienes and Allylic Systems

Cycloalkanes Synthesis and Properties

Ch. 10 – Conjugation in Alkadienes and Allylic Systems

12/7/2018 CHEM 240 PRINCIPLES OF ORGANIC CHEMISTRY (I) FOR BSc’s STUDENTS IN CHEMISTRY PROGRAM, COLLEGE OF SCIENCE PRE-REQUISITES COURSE; CHEM 107 CREDIT.

Guillaume Barbe Guillaume Pelletier Miguel St-Onge Sébastien Vanier

Proposal: Total Synthesis of Biyouyanagin A

Introduction to Mass Spectrometry (MS)

Cycloalkanes Synthesis and Properties

Fragmentation of M+ Draw structure of M+ if possible and then draw possible heterolytic cleavages (curved arrows) or homolytic cleavages (fish hooks)

Pericyclic Reactions Carey & Sundberg: Part A; Chapter 11

Based on McMurry’s Organic Chemistry, 7th edition

Based on McMurry’s Organic Chemistry, 7th edition

Cycloalkanes Synthesis and Properties

Advanced Organic Synthesis

Cycloalkanes Synthesis and Properties

Kiyoun Lee and Dale L. Boger*

DIVERGENT TOTAL SYNTHESES OF LYCONADINS A AND C

Chapter 23 Substitution Reactions of Carbonyl Compounds

Based on McMurry’s Organic Chemistry, 7th edition

Conjugated Dienes and U.V. Spectroscopy

Facile Diels-Alder Reactions with Pyridines Promoted by Tungsten

Oxidative Addition, Reductive Elimination

Fragmentation of M+ Draw structure of M+ if possible and then draw possible heterolytic cleavages (curved arrows) or homolytic cleavages (fish hooks)

Presentation transcript:

Synthesis of Biyouyanagin A Introduction Synthesis of Biyouyanagin A Philippe Murphy Daniel Beaudoin Lucie Zimmer Christian Perreault Capt’n Alex

Retrosynthesis p-Allyl Substitution Enolate C-Acylation

Retrosynthesis p-Allyl Substitution Enolate C-Acylation Radical Allylation

Retrosynthesis p-Allyl Substitution Enolate C-Acylation C-H Insertion Radical Allylation O-Alkylation

Retrosynthesis p-Allyl Substitution Enolate C-Acylation C-H Insertion Radical Allylation O-Alkylation Diels-Alder Suzuki Coupling

Preparing the Diels-Alder 1 Xu, D.; Li, Z.; Ma, S. Tetrahedron Lett. 2003, 44, 6343

Preparing the Diels-Alder 1 Xu, D.; Li, Z.; Ma, S. Tetrahedron Lett. 2003, 44, 6343 2 Smith, N. D.; Goodman, M. Org. Lett. 2003, 5, 1035 3 (DHQD)2-PHAL and K2OsO2(OH)4

Diels-Alder key step

Diels-Alder key step

Diels-Alder key step

Why the D-A should work

Diels-Alder key step

Retrosynthesis C-H Insertion O-Alkylation

Tetrahydrofuran Ring-Closure

Tetrahydrofuran Ring-Closure

Retrosynthesis p-Allyl Substitution Radical Allylation

Cyclobutane Formation

Double Bond Reduction

Double Bond Reduction

Retrosynthesis p-Allyl Substitution Enolate C-Acylation

Putting the Side Chain in Place

Final Cyclization

Final Cyclization

Retrospective 19 Steps in Total!