"Shaun the Alcohol": Molecular Design Brings a Cartoon Character Alive
Keywords:
molecular design, Shaun the Ether, cyclization, Corey-Chaykovsky reactionAbstract
Molecular design is a crucial and interesting issue in Organic Chemistry governing both novel molecular and development of new synthesis route. In this work, we successfully brought a lovely comic character “Shaun the Sheep” into reality through molecular design. This novel molecular, which we named “Shaun the Alcohol”, has a cycloheptane “body”, an ethylene oxide “head”, four methyl “feet” and an oxhydryl “tail”. With a special macrocyclic, cyclic ether and branched structure, “Shaun the Alcohol” is expected to become an important reaction intermediate.
References
Sakai, T.; Nagao, Y.; Nakamura, Y.; Mori, Y. ACS Omega 2017, 2 , 8543-8549.
Chanteau, S. H.; Tour, J. M. J. Org. Chem. 2003, 68, 8750-8766.
Vives, G.; Kang, J. H.; Kelly, K. F.; Tour, J. M. Org. Lett. 2009, 11, 5602-5605.
Kurissery, A. T.; Rajkumar, G. A.; Arvapalli, V. S.; Pitchumani, V. Tetrahedron Lett. 2017, 58, 3607-3611.
Ogiyama, T.; Inoue, M.; Honda, S.; Yamada, H.; Watanabe, T.; Gotoh, T.; Kiso, T.; Koakutsu, A.; Kakimoto, S.; Shishikura, J.-i. Bioorg. Med. Chem. 2014, 22, 6899-6907.
Yu, H.; Deng, X.; Cao, S.; Xu, J. Lett. Org. Chem. 2011, 8, 509-514.
王积涛; 王永梅; 张宝申; 胡青眉; 庞美丽, 有机化学, 第三版.; 南开大学出版社: 天津, 2009, pp 534.
Dong, G.; Yuan-Dong, L.; Hong-Jiang, S.; Li-Dong, W.; Yang, W.; Cheng-Lu, Z. Chinese J. Appl. Chem. 2009, 26, 1301-1304.
Mori, K.; Mori, H. Tetrahedron 1985, 41, 5487–5493.
Krief, A.; Laboureur, J. Tetrahedron Lett. 1987, 28, 1545-1548.
Clarembeau, M.; Cravador, A.; Dumont, W.; Hevesi, L.; Krief, A.; Lucchetti, J.; Van Ende, D. Tetrahedron 1985, 41, 4793-4812.
Thieme Group. Science of Synthesis Web. https://science-of-synthesis.thieme.com, 26.3 product class 3 (Cyclopropanones and Their Precursors)(accessed July 16, 2022).