Peng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 18860-18867.
In 2004, the first purified crystal of maoecrystal V was obtained from a natural vegetal source. Motivated by the potential for discovering new antimitotic agents, Peng & Danishefsky designed a program in which they were able to successfully carry out the total synthesis of maoecrystal V. They accomplished this by basing their research on trial & error, advanced chemical analysis, and knowledge gained from the prior research in the field. Their final plan for total synthesis consists of several key steps, namely an intramolecular Diels-Alder cyclization reaction and an intramolecular hydrogen transfer, which results in the fusion of two of the rings present in the chemical structure of maoecrystal V.
"After spending countless hours in the lab researching complex synthetic schemes, one can easily feel isolated from the rest of the world. The members of SSG 1, however, avoid this problem by taking to social media! As self-proclaimed social media experts, we will gladly show you how to stay sane by combining your chemistry research with the latest hot gossip on your Facebook & Twitter feeds. So, charge up your smartphone, grab your selfie-stick, and join SSG 1 as we use social media to
procrastinate solve some of chemistry's most challenging problems!"
Zheng, C.; Dubovyk, I.; Lazarski, K. E.; Thomson, R. J. J. Am. Chem. Soc. 2014, 136, 17750-177567.
Maoecrystal V, a cytotoxic and polycyclic diterpene, is synthesized enantioselectively and described in this article, utilizing reactions such as an intramolecular Heck reaction, an oxidative cycloetherification, and an intermolecular Diels-Alder reaction. N-H and C-H oxidation is used later in the synthesis process to insert the desired functional groups to complete the product.
"Come along on a magical adventure as you make your way through the toughest courses at the Hogwarts School of Witchcraft and Wizardry! Pay close attention as various professors guide you through Transfiguration, Potions, Defense Against the Dark Arts, and Care for Magical Creatures to success in your O.W.L.s (Organic Wizarding/Witchcraft Levels) and N. E. W. T. S. (Next Echelon Wizarding/Witchcraft Tests in Synthesis)! "
Gong, J.; Lin, G.; Sun, W.; Li, C.-C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745-16746.
Maoecystal V has previously been isolated from a Chinese medical herb, Isodon eriocalx. It has been shown to inhibit HeLa cells, suggesting it has anti-tumor properties. Maoecrystal V contains a fascinating penacyclic framework. For these reasons, there is a need for an efficient synthesis strategy. Here, the authors describe the first total synthesis of maoecrystal V.
"After an exhausting day in SSG, there's nothing better than coming home and watching some of your favoite classic cartoon television shows! Kick back with the members of SSG 3 as they give you a tour of the classics: Spongebob Squarepans, Winnie the Pooh, Kim Possible, the Magic School Bus, Dora the Explorer, and the Powerpuff Girls."
Lu, P.; Mailyan, A.; Gu, Z.; Guptill, D. M.; Wang, H.; Davies, H. M. L.; Zakarian, A. J. Am. Chem. Soc. 2014, 136, 17738-17749.
In SSG 4's paper, the development of a program concerned with the enantioselective total synthesis of maoecrystal V (a highly modified ent-kauranoid) is described. An early stage chiral auxiliary-directed asymmetric C−H functionalization for the construction of a key intermediate enabled the first asymmetric synthesis of the natural enantiomer of maoecrystal V, confirming the assigned stereochemistry. An unconventional central intramolecular Diels−Alder reaction, which is dependent on the properties of the dienophile, led to the development of a surprise maoecrystal V, which this paper calls maoecrystal ZG. Since maoecrystal V was found to be cytotoxic, the cytotoxic properties of maoecrystal ZG were also investigated.
" Join SSG 4 as we take a trip "around the world"...of maoecrystal chemistry!!! "
Su, S.; Rodriguez, R. A.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 13922-13925.
The bioactive pyrrole-imidazole marine alkaloid (PIA) family of molecules contains axinellamines A and B, massadine, massadine chloride, and palau?amine, all of which have a common chemical progenitor. The prior synthesis of this progenitor was inefficient, but was largely refined by the group to allow for scalable syntheses of the PIA family, namely axinellamines A and B. By means of their research, three methodological advances were also made, involving an ethylene glycol-assisted Pauson-Khand cycloaddition reaction to minimize decomposition, a chemoselective In/Zn-mediated Barbier-type reaction to allow for effective desymmetrization, and a stereocontrolled TfNH2-assisted chlorination-spirocyclization reaction.
"These chemical discoveries are astounding, but were they actually made by aliens? Was the laboratory located in a high-security research facility in the middle of the desert? Are there connections with these reactions and a secret society?s plot to take over the world? Who knows!? ? Grab your shoddy video recorder and Nana?s old Polaroid camera and join SSG 5 as we delve into the realm of conspiracy theories!"
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