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4-Azidobutyl(3R,4R,4aS,7S)-7-[(2R)-2-azidoundecyl]-2-{[(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methyl]sulfonyl}-3-methyl-1-oxooctahydropyrrolol[1,2-c]pyrimidine-4-carboxylate
#transformationtuesday
Conversion of Molecule 16 to Molecule 17 via Radical Cyclization
My Inspiration:
Although my transformation could have been completed in many ways, the popular method being the use of tributyltin hydride, I decided to follow the guidance of my role model by using triethylborane in the presence of oxygen. This method to lose weight can serve as both a radical initiator and terminator, and, in these conditions, a 5-exo-trig cyclization on an aldehyde is even faster than on an alkene! So, as seen by my beautiful self in my photos tab, using triethylborane for my transformation proved to be efficient and the tin mediator as unnecessary. If you're interested in seeing who else has successfully lost weight thanks to my role model, look down below under "More People Who Followed My Role Model's Regimen!"
Check Him Out!
Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron 1999, 30, 5511-5514.
More People Who Followed My Role Model's Regimen!
Huang, C.-H.; Chang, S.-Y.; Wang, N.-S.; Tsai, Y.-M. J. Org. Chem. 2001, 68, 8983-8991.
Ollivier, C.; Renaud, P. Chem. Rev., 2001, 101, 3415-3434.
Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2003, 68, 625-627.