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Title

"Total Synthesis of (-)-Sarain A"

Reaction Scheme

“Total Synthesis of (-)-Sarain A” Becker, M. H.; Chua,P.; Downham, R.; Douglas, C. J.; Garg, N.K.; Hiebert, S.; Jaroch, S.; Matsuoka, R.T.; Middleton, J. A.; Ng, F.W.; Overman, L. E. J. Am. Chem. Soc. 2007, 129, 11987-12002.  is an article outlining the long and challenging task of synthesizing Sarain A. This molecule, isolated from the marine sponge Reniera sarai, has captivated organic chemists because of itscomplex structure which includes a 14 member ring and a tertiary amine-aldehyde interaction. Molecules 139 and 140, shown below are intermediates, in this synthesis.

 

"Chemistry is an average subject that no one understands
Heat and Light and Energy always giving it commands
But gloom and doom up in the lab
Is broken instantly
By some magic little reagents who grant our every wish
'Cause in reality they are our
Odd reactions, fairly odd reactions
Beakers and Flasks,
and impossible tasks,
Odd reactions, fairly odd reactions
Can’t Stop, Really hot, Didn’t mean to drop that,
Use tongs, Like those songs, hey put your goggles on
IBX, THF, Br2, DCC!
Odd reaction, fairly odd reaction
It flips your lid when you are a kid with fairly odd reactions!
Yeah, right!"

By: Jess Martens, Sahar Rahmani, Lauren Heath