Synthesis of Marine Alkaloids from the Oroidin Family
We found 3 chemistry papers in journals that have similar mechanistic steps to the step that that we are investigating in this website. We will explore one of these papers below:
Paper 1: Arndt, H.-D.; Riedrich, M. Angewandte Chemie 2008, 47, 4785-4768.
In 2008, Hans-Dieter Arndt and Matthias Riedrich studied the synthesis of alkaloids from the oroidin family, including Sceptrin, the product of 
our assigned transformation. They concluded that dimerization of Oroidin 6 produced the backbone for the alkaloids and following functionalization created Sceptrin and the other marine alkaloids shown here. All of these molecules are densely functionalized and highly oxidized. The similarity of these alakoids and the fact that they often occur simultaneously hints at the probability of a common biosynthetic precursor, such as 6.The similarity of these alakoids and the fact that they often occur simultaneously hints at the probability of a common
biosynthetic precursor, such as 6. They tested this hypothesis and were able to synthesize these complex alkaloids. Another hypothesis of biosynthesis was proposed by a different team, and includes cycloaddition to make the six-membered ring compounds. This method was also successful, but is less likely to occur in vivo. In the synthesis that our assigned paper follows, sceptrin is induced to high-temperature conditions and a double-ring enlargement occurs. This is another acceptable way to produce these compounds in the lab, but dimerization is the most likely pathway that these marine alkaloids are synthesized in nature.
Paper 2: Al Mourabit, P. Portier, Eur. J. Org. Chem. 2001, 237-243.
Paper 3: Wei, Y.: Zipse, H. Eur. J. Org. Chem. 2008, 22, 3811-3816.