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To our visitors from outside the Chemistry 215H course:


The documents linked below were solely generated by a class-wide collaboration between the second-term first year students in the honors section of Chemistry 215/216 during the Winter, 2010 Term. The assignments that resulted in these pages were designed in collaboration with the five junior/senior undergraduate leaders who are pictured below. You can find out more details about how these pages are created, and the Structured Study Group program in general, by referencing other parts of the Chemistry 215H/216H web site.

Tutorials

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Dr. Koreeda

Thursdays 7:00-9:00pm

Trost, B. M; Dont, G. J. Am. Chem. Soc. 2010, 132, 16403-16416.

Asymmetric total synthesis of bryostatin 16 was achieved in 26 steps in the longest linear sequence and in 39 total steps from aldehyde 10. A Pd-catalyzed alkyne-alkyne coupling was employed for the first time as a macrocyclization method in a natural product synthesis. A route to convert bryostatin 16 to a new family of bryostatin analogues was developed. Toward this end, 20-epi-bryostatin 7 was synthesized from a bryostatin 16-like intermediate; the key step involves a Re-catalyzed epoxidation/ring- opening reaction. Preliminary biological studies indicated that this new analogue exhibits nanomolar anti- cancer activity against several cancer cell lines.

Chen

 

"Of all the great monuments both natural and man-made in history, the new 7 wonders of the world are the most impressive. Experience the myth and legend of Chichen-Itza, the beauty of Machu Pichu, the majesty of the Taj Mahaj, the spirit of Christ the Savior, the grand Coliseum and glorious Petra. Come with us to explore the chemistry behind these masterpieces of history."


Wednesdays 5:00-7:00pm

Keck, G.; Poudel, Y. B.; Cummins, T. J.; Rudra, A.; Covel, J. A. J. Am. Chem. Soc. 2011, 133, 744-747.

The bryostatins are chemical compounds of intense study for their potential therapeutic activities that target a variety of cancers in humans. Particularly, bryostatin 1 holds promise as a potent drug agent against a variety of other prevalent diseases such as Alzheimer’s disease. Keck et al. at the University of Utah propose the first total synthesis of bryostatin 1 by preparation and annulation of pyran derivatives.

Iyer

 

"Before the age of electronics took hold of the younger generation, there was the golden age of marbles, jigsaw puzzles, and board games. Join Mr. Pennybags, Gloppy the Chocolate Monster, Colonel Mustard, and the rest of SSG 2 as we reinvigorate our youthful mirth and old family game night memories with four timeless board game classics. Put away the Wii controller, turn off your smart phones, put your organic chemistry thinking cap on, and join us on a throwback to the games that kept us entertained in the ‘90s!"


Wednesdays 7:30-9:30pm

Levin, S.; Nani, R. R.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 774-776.

(+)-Salvileucalin B, originally isolated from Salvia leucantha by Takeya, is synthesized here by Levin et al. in an 18 step synthesis. Synthetic techniques such as the Arndt-Eistert homologation as well as the formation of a fully substituted cyclopropane ring by use of a copper catalyst were utilized in this total synthesis, leading to advancements in the study of metal catalyzed cyclopropanation.

Gildenberg

 

"Join SSG 3 on our action packed, video game adventure through the world of organic chemistry! Smash attack your enemies and solve mechanisms with Super Smash Bros., solve the puzzle of NMR and save princess Zelda with Link, avoid the ghosts and tackle leading questions with pac man, and complete quests and explore experimental procedures in World of Warcraft as we embark on our journey through the synthesis of Salvileucalin B."


Thursdays 5:00-7:00pm

Koizumi, H.; Yokoshima, S.; Fukuyama, T. Chem. Asian J. 2010, 5, 2192-2198.

Morphine is one of the most widely used and dirt-cheap drugs throughout the world. It is universally administered for the treatment of pain in spite of its extreme addictive affects. For years, researchers have wanted to find suitable, cheap alternates to morphine minimizing the negative side-effects. A pioneer of this work is Fukuyama, who has been working diligently to find morphine mimics. Before this can be established, an efficient and modular total synthesis must be discovered to create a large library of potential compounds with high activity while reducing the costs. Fukuyama took another step toward realizing this with his novel synthesis of morphine utilizing the methods in the front lines of advanced organic chemistry.

Grillo

 

"Contrary to the hearsay of older generations, today's youth are connected more with reality than ever before. While we watch parents struggle to turn on a computer and check email, we are simultaneously texting, surfing the web, dancing to an iPod, watching TV, and pretending to actually work on that nuisance of a homework assignment from that ancient professor. The producers of SSG 4 decided that it was about time to entertain the world depicting the day to day activities of the college student. We quickly realized that of course no other venue demonstrates this better than reality shows! So sit, relax, and see what the Michigan Difference really is: doing some crazy, stupid, and potentially deadly things with Bear Grylls while scaring the hell out of others with Fear Factor, satisfying those late Saturday night cravings with Top Chef and Cake Boss, and finally grabbing that new outfit from American's Next Top Model because IT'S T-SHIRT TIME, and its time to rage like a bro, pump your fist, and avoid that grenade right around the corner or find that juiced-up gorilla poofing your hair in the air. Even with this hectic schedule, the students of Tony's SSG still find time to become masters of chemistry. The Michigan Difference."


Nicolaou, K. C.; Tria, G. S.; Edmonds, D. J.; Kar, M. J. Am. Chem. Soc. 2009, 131, 15909-15917.

Thursdays 7:00-9:00pm

Pragani et al. report the first total synthesis of the Zwitterionic Polysaccharide (ZPS) A1 repeating unit in this publication. ZPSs have been demonstrated to stimulate an immune system response via T-cell major histocompatibility II presentation, whereas most bacterial capsular polysaccharides do not. The ZPS A1 has been shown to have promising immunostimulatory activity, and is thus useful for practical applications such as vaccines. Here, the authors present the first total synthesis of the ZPS A1 repeating unit, providing easier research on this compound.

Li

 

"The students of Han’s 215HH SSG are at a relaxing vacation in Disney World, enjoying some great scenery and movie themed attractions. Suddenly, after getting off that awesome spinning teacup ride, they see an evil army of minions invading the park and wreaking general havoc! When interrogated by a daring student of the class, one of the minions breaks down and admits that the army is led by a diabolical chemist, who has inoculated the army with bacteria in hopes of infecting the unsuspecting Disney characters. Luckily, the students in SSG remember that Pragani et al. have recently discovered how to synthesize Zwitterionic Polysaccharide A1 repeating unit, an immunomodulatory agent that can activate the T-cell dependent immune response through MHC II presentation. Follow the brave students in their quest to read the literature, synthesize the polysaccharide, and prevent utter chaos from being unleashed!"


 

Website by Eric Chen. Style copyright © 2010 The Regents of the University of Michigan.