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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, 2012 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

Wednesdays 5:00-7:00pm

Mendoza, A.; Ishihara, Y.; Baran, P. S. Nature Chem. 2011, 4, 21-25.

Taxanes are a large class of organic compounds produced by plants, the most famous of which, Taxol, is an anti-cancer drug used to treat lung, liver, ovarian, and breast cancers. In this paper, Mendoza et al. describe the first practical and scalable synthetic pathway for the preparation of (+)-taxa-4(5),11(12)-dien-2-one, which has a key functional handle which can be altered to synthesize oxidized members of the taxane family. The 7 step synthesis involves a Diels-Alder scheme to introduce the 6-8-6 tricyclic system that is characteristic of the taxane family. The synthesis of this building block to oxidized taxanes is a critical step for further synthesis of members of the taxane family.

Sarah

 

"Animated movies hold a special place in the hearts of SSG 1. Join us as we remember the classics and explore newer releases in our mission to understand the synthesis of (+)-taxa-4(5),11(12)-dien-2-one. Sit back, relax, and enjoy the show as SSG 1 presents Ponyo, Up, Toy Story, Beauty and the Beast, Pokémon, Howl’s Moving Castle and Aladdin."


Wednesdays 7:00-9:00pm

Shimokawa, J.; Harada, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 17634-17637.

Here, Shimokawa et. al. report the first total synthesis of gelsemoxonine. Gelsemoxonine, discovered in 1994, is a monoterpenoid indole alkaloid and those alkaloids have provided a benchmark for state-of-the-art synthetic strategies due to their complex, compact, and strained structures. The synthesis of gelsemoxonine here utilized a novel divinylcyclopropane-cycloheptadiene rearrangement, as well an isomerization reaction of the unsaturated aldehyde to the saturated ester via the TMSCN-DBU reagent combination. The motivation of this synthesis was partially due to gelsemoxonine's cytotoxic potential, but primarily as a way of introducing novel techniques to the synthesis of alkaloids.

Ben

 

"Join Harry Potter and members of Ben’s SSG as they seek to uncover the mysteries behind the synthesis of gelsemoxonine! Just as Harry Potter discovered something new each year he was at Hogwarts, the students of SSG 2 uncovered the mysteries and explored the chemistry behind seven reactions in this article."


Wednesdays 7:30-9:30pm

Cha, J. Y.; Yeoman, J. T. S.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964-14967.

Maoecrystal Z is a natural product found in the Chinese medicinal herb Isodon eriocalyx. It is related to other natural products, all of which contain a central spiro-fused lactone, that have been shown to exhibit antitumor activity and cytotoxicity towards various cancer cell lines. Here, Cha et al. synthesize (-)-Maoecrystal Z in a twelve step synthesis involving a diastereoselective Ti(III)-mediated reductive epoxide coupling reaction as well as a diastereoselective Sm(II)-mediated reductive cascade cyclization reaction.

Melissa

 

"A wild Maoecrystal appeared! Break out your shiny Charizard and your level 100 Blastoise- We're going to need all the help we can get! Join Ash and the rest of SSG 3 on our journey through Kanto as we synthesize Maoecrystal Z. Look at some NMR in Cerulean City and Viridian City, watch a mechanism at Saffron City and Cinnabar Island, read experimentals at Vermilion City and Fuchsia City, or just explore with your Pokemon and get yourself into some intense battles with the greatest gym leaders around. Gotta catch 'em all!"


Thursdays 5:00-7:00pm

Tanino, K.; Takahashi, M.; Tomata, Y.; Tokura, H.; Uehara, T.; Narabu, T.; Miyashita, M. Nature Chem. 2011, 3, 484-488.

Solanoeclepin A is the key hatch-stimulating substance for the potato cyst nematode, a troublesome parasite that lives on and destroys its host vegetable plant. A method used to fight these parasites is to stimulate early hatching, but the key hatching stimuli are not naturally available in large enough quantities to support this method. This article offers the first chemical synthesis of solanoeclepin A. The crucial steps in this chemical synthesis include an intramolecular cyclization reaction and an intramolecular Diels-Alder reaction. The synthesis of solanoeclepin A may be used to contribute to an important food issue facing over 50 countries.

Nicole

 

"Learning about the synthesis of solanoeclepin A can be fun and entertaining, thanks to the playful spirit of SSG 4! Take a look in our closet of games, which includes Clue, Sequence, Ninja Game, Candy Land, Chess, Mario Party, Risk, Monopoly, and Life."


Thursdays 7:00-9:00pm

Kong, K.; Moussa, Z.; Lee, C.; Romo, D. J. Am. Chem. Soc. 2011, 133, 19844-19856.

The study and synthesis of marine toxins provides valuable insight into the causes of food poisoning in humans, particularly with respect to its biological and pharmacological interactions with the human nervous system. The spirocyclic imine is an important marine toxin class recently isolated in coasts around the globe and associated with numerous instances of food poisoning; this toxin class thus poses particularly widespread concerns with regard to seafood safety. Kong et al. report the first complete synthesis of the spirocyclic imine (-)-gymnodimine via a convergent process involving a novel intramolecular Barbier reaction. The process reported here allows for the creation of various other gymnodimine analogues, facilitating deeper studies of this class of marine toxin.

Nikhil

 

"For many of today’s undergraduates, the ‘90s were the golden age of Discman, Pokémon, Beanie Babies, and dial-up Internet. If anything is apparent about the ‘90s, besides the discolored jeans and cheap gas prices, it is the vast collection of TV classics. It has been a couple decades, but I think we all still smile as we catch some of those reruns late at night. So join SSG 5 as we embark on a journey through the unforgettable cartoons of the ‘90s, relive our childhood years, and observe some interesting chemistry along the way!"


 

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