Dakin Oxidation

Ciguatoxin

Total Synthesis of Ciguatoxin
Akinari Hamajima and Minoru Isobe
Angew. Chem. Int. Ed., 2009, Early View
DOI: 10.1002/anie.200805996

For THURSDAY, March 26

Nagelamide D

Total Synthesis of the Putative Structure of Nagelamide D
Manojkumar R. Bhandari, Rasapalli Sivappa and Carl J. Lovely
Org. Lett., 2009, ASAP
DOI: 10.1021/ol9001762

For Friday, March 20.

Stille-Kelly Coupling

The Pd-catalyzed intramolecular biaryl coupling of aryl halides or aryl triflates in the presence of the distannanes.

Phomactin A

Total Synthesis of Phomactin A
Yu Tang, Kevin P. Cole, Grant S. Buchanan, Gang Li and Richard P. Hsung
Org. Lett., 2009, ASAP
DOI: 10.1021/ol900237e

For Friday, March 13th.

Ciamician-Dennstedt Rearrangement

(a.k.a. the "abnormal" Reimer-Tiemann)

The rearrangement of pyrroles to 3-halo-pyridines upon treatment with haloforms in the presence of a strong base.

Jones Oxidation

The chromic acid oxidation of primary and secondary alcohols to carboxylic acids and ketones.

Sporolide B

Total Synthesis of Sporolide B
K. C. Nicolaou, Yefeng Tang, and Jianhua Wang
Angew. Chem. Int. Ed., 2009, early view
DOI: 10.1002/anie.200900264

To be discussed THURSDAY, March 5th.

Baylis-Hillman Reaction

The formation of a C-C single bond between the alpha-position of conjugated carbonyl compounds, such as esters and amides, and carbon electrophiles, such as aldehydes and activated ketones in the presence of a suitable nucleophilic catalyst, particularly a tertiary amine.

Norhalichondrin B

A Total Synthesis of Norhalichondrin B
Katrina L. Jackson, James A. Henderson, Hajime Motoyoshi, Andrew J. Phillips
Angew. Chem. Int. Ed., 2009, early view
DOI: 10.1002/anie.200806111

Reimer-Tiemann Reaction

The formylation of phenols and heterocyclic phenols using chloroform in an aqueous alkaline medium.

Stetter Reaction

The addition of aliphatic and aromatic aldehydes across activated double bonds in the presence of a nucleophilic catalyst.

(−)-Kendomycin

Total Synthesis of (−)-Kendomycin
Jason T. Lowe and James S. Panek
Org. Lett., 2008, 10 (17), pp 3813–3816
DOI: 10.1021/ol801499s

Tsuji-Trost Allylation

The Pd-catalyzed allylation of carbon nucleophiles with allylic compounds via pi-allylpalladium complexes

Chlorosulpholipid cytotoxin

Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning
Christian Nilewski, Roger W. Geisser and Erick M. Carreira
Nature, 2009, 457, pp 573-577
DOI: 10.1038/nature07734

Eschenmoser Methenylation

The introduction of a (dimethylamino)methyl group into the alpha-position of a carbonyl group using dimethyl(methylene)ammonium iodide (Eschenmoser's salt), followed by an elimination to the corresponding alpha-methylene carbonyl compound.

Bryostatin 16

Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches
Barry M. Trost and Guangbin Dong
Nature, 2008, 456, pp 485-488
DOI:10.1038/nature07543

Brevetoxin A

Total Synthesis of Brevetoxin A
Michael T. Crimmins, J. Lucas Zuccarello, J. Michael Ellis, Patrick J. McDougall, Pamela A. Haile, Jonathan D. Parrish and Kyle A. Emmitte
Org. Lett., 2009, 11 (2), pp 489–492
DOI: 10.1021/ol802710u

Myers Asymmetric Alkylation

The alkylation of N-acylated pseudoephedrines to obtain enantiomerically enriched alpha-alkylated aldehydes, ketones, carboxylic acids, and alcohols.

Total Synthesis of GEX1A
Timothy J. Murray and Craig J. Forsyth
Org. Lett., 2008, 10 (16), pp 3429–3431
DOI: 10.1021/ol800902g

Rubottom Oxidation

The alpha-hydroxylation of carbonyl compounds via the peroxyacid oxidation of the corresponding silyl enol ethers.

The Total Synthesis of (±)-Rishirilide B
John G. Allen and Samuel J. Danishefsky
J. Am. Chem. Soc., 2001, 123 (2), pp 351–352
DOI: 10.1021/ja003272a

Total Synthesis of FR901464. Convergent Assembly of Chiral Components Prepared by Asymmetric Catalysis
Christopher F. Thompson, Timothy F. Jamison, and Eric N. Jacobsen
J. Am. Chem. Soc., 2000, 122 (42), pp 10482–10483
DOI: 10.1021/ja0055357

Sharpless Asymmetric Aminohydroxylation

Stereocontrolled Total Synthesis of (−)-Ephedradine A (Orantine)
Wataru Kurosawa, Toshiyuki Kan, and Tohru Fukuyama
J. Am. Chem. Soc., 2003, 125 (27), pp 8112–8113
DOI: 10.1021/ja036011k

Sharpless Asymmetric Dihydroxylation

The asymmetric reaction of osmium tetroxide with olefins to give cis vicinal diols in the presence of a chiral tertiary amine ligand.

Total Synthesis of Neooxazolomycin
Evans Otieno Onyango, Joji Tsurumoto, Naoko Imai, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
Angew. Chem. Int. Ed., 2007, 46 (35), pp 6703-6705
DOI: 10.1002/anie.200702229

(From 09/26/08)

Petasis Boronic Acid-Mannich Reaction

The formation of allylic amines based on a modified Mannich reaction where vinylboronic acids serve as the nucleophilic component.

Formal total synthesis of (-)-haouamine A
Alois Fürstner and Jens Ackerstaff
Chem. Commun., 2008, pp 2870-2872
DOI: 10.1039/b805295f

(From 09/19/08)

Weinreb Ketone Synthesis

The synthesis of ketones from N-methoxy-N-methylamides (Weinreb's amides) with organometallic reagents.

Formal Total Synthesis of RK-397 via an Asymmetric Hydration and Iterative Allylation Strategy
Haibing Guo, Matthew S. Mortensen and George A. O’Doherty
Org. Lett., 2008, 10 (14), pp 3149–3152
DOI: 10.1021/ol801055b

(From 09/05/08)

Wagner-Meerwein Rearrangement

The generation of a carbocation followed by the [1,2]-shift of an adjacent carbon-carbon bond to generate a new carbocation.

Concise Means for Accessing an Advanced Precursor to 1-Deoxypaclitaxel
Xin Guo and Leo A. Paquette
J. Org. Chem., 2005, 70 (1), pp 315–320
DOI: 10.1021/jo048289g

Ring expansion of 11H-benzo[b]fluorene-11-methanols and related compounds leading to 17,18-diphenyldibenzo[a,o]pentaphene and related polycyclic aromatic hydrocarbons with extended conjugation and novel architectures
Yonghong Yang, Weixiang Dai, Yanzhong Zhang, Jeffrey L. Petersen, and Kung K. Wang
Tetrahedron, 2006, 62, pp 4364-4371
DOI: 10.1016/j.tet.2006.02.066

Mitsunobu Reaction

The substitution of primary and secondary alcohols with nucleophiles in the presence of a dialkyl azodicarboxylate and a trialkyl- or triaryl phosphine.

First Total Syntheses of (±)-Annuionone B and (±)-Tanarifuranonol
Hui-Yi Shiao, Hsing-Pang Hsieh, and Chun-Chen Liao
Org. Lett., 2008, 10 (3), pp 449–452
DOI: 10.1021/ol7028178

(From 08/22/08)

Kolbe-Schmitt

The preparation of ortho- or para-substituted aromatic hydroxy acids from the corresponding phenols under basic conditions using carbon dioxide.

A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies
Aideen M Dunne, Stefan Mix, and Siegfried Blechert
Tetrahedron Lett., 2003, 44 (13), pp 2733-2736
DOI: 10.1016/S0040-4039(03)00346-0

Anthranilamide inhibitors of factor Xa
David Mendel, Angela L. Marquart, Sajan Joseph, Philip Waid, Ying K. Yee, Anne Louise Tebbe, Andrew M. Ratz, David K. Herron, Theodore Goodson, John J. Masters, Jeffry B. Franciskovich, Jennifer M. Tinsley, Michael R. Wiley, Leonard C. Weir, Jeffrey A. Kyle, Valentine J. Klimkowski, Gerald F. Smith, Richard D. Towner, Larry L. Froelich, John Buben and Trelia J. Craft
Bioorg. Med. Chem. Lett., 2007, 17, pp 4832-4836
DOI:10.1016/j.bmcl.2007.06.051

Lossen Rearrangement

The conversion of O-acyl hydroxamic acids to the corresponding isocyanates.

Specific degradation of pectins via a carbodiimide-mediated Lossen rearrangement of methyl esterified galacturonic acid residues
Paul W. Needs, Neil M. Rigby, Stephen G. Ring, and Alistair J. MacDougall
Carbohydr. Res., 2001, 333 (1), pp 47-58
Link to PDF

Improved Synthesis of a New Nonpeptidic Inhibitor of Human Neutrophil Elastase
Kazuyuki Ohmoto, Tetsuya Yamamoto, Toshihide Horiuchi, Tsutomu Kojima, Katsutoshi Hachiya, Shinsuke Hashimoto, Masanori Kawamura, Hisao Nakai, and Masaaki Toda
Synlett, 2001, 2001 (2), pp 299-301
Link to PDF

Staudinger Reaction

The reaction of organic azides with trivalent phosphorous compounds (e.g., trialkyl- or triarylphosphines) to afford the corresponding aza-ylides.

Enantioselective Synthesis of Marine Indole Alkaloid Hamacanthin B
Biao Jiang, Cai-Guang Yang, and Jun Wang
J. Org. Chem., 2002, 67 (4), pp 1396–1398
DOI: 10.1021/jo0108109

A FRET-Based Fluorogenic Phosphine for Live-Cell Imaging with the Staudinger Ligation
Matthew J. Hangauer and Carolyn R. Bertozzi
Angew. Chem. Int. Ed., 2008, 47 (13), pp 2394-2397
DOI: 10.1002/anie.200704847

Quasi-Favorskii

The skeletal rearrangement of alpha-halo ketones, with no hydrogen atom at the alpha'-position or bicyclic alpha-halo ketones with an alpha'-hydrogen atom at the bridgehead carbon atom, upon treatment with a nucleophile.

The [4 + 3]-Cycloaddition/Quasi-Favorskii Process. Synthesis of the Carbocyclic Core of Tricycloclavulone
Michael Harmata and Sumrit Wacharasindhu
Org. Lett., 2005, 7 (13), pp 2563–2565
DOI: 10.1021/ol050598l

Hajos-Parrish

The amino acid catalyzed intramolecular aldol reaction of prochiral 2-alkyl-2-(3-oxoalkyl)-cyclopentane-1,3-diones.

An Unconventional Approach to the Enantioselective Synthesis of Caryophylloids
Oleg V. Larionov and E. J. Corey
J. Am. Chem. Soc., 2008, 130 (10), pp 2954–2955
DOI: 10.1021/ja8003705

A Short Enantioselective Total Synthesis of the Third-Generation Oral Contraceptive Desogestrel
E. J. Corey and Alan X. Huang
J. Am. Chem. Soc., 1999, 121 (4), pp 710–714
DOI: 10.1021/ja983179a

Jacobsen Hydrolytic Kinetic Resolution

The use of Co(III)salen complexes to catalyze the reaction of racemic terminal epoxides with water to afford highly enantiomerically enriched terminal epoxides and diols.

Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic Kinetic Resolution of Terminal Epoxides
Lars P. C. Nielsen, Christian P. Stevenson, Donna G. Blackmond, and Eric N. Jacobsen
J. Am. Chem. Soc., 2004, 126 (5), pp 1360–1362.
DOI: 10.1021/ja038590z

Enantioselective Synthesis of an All-syn Four Vicinal Fluorine Motif
Luke Hunter, David O'Hagan, and Alexandra M. Z. Slawin
J. Am. Chem. Soc., 2006, 128 (51), pp 16422–16423
DOI: 10.1021/ja066188p

Finkelstein Reaction

The equilibrium exchange of the halogen atom in alkyl halides for another halogen atom.

Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction
Artis Klapars and Stephen L. Buchwald
J. Am. Chem. Soc., 2002, 124 (50), pp 14844–14845
DOI: 10.1021/ja028865v

A novel approach for the synthesis of the peripheral benzodiazepine receptor ligand, PK11195
Louise Stevenson, Sally L. Pimlott and Andrew Sutherland
Tetrahedron Lett., 2007, 48 (40), pp 7137-7139
DOI: 10.1016/j.tetlet.2007.07.203

(From July 4, 2008)