Studies towards the synthesis of Chartelline C and related alkaloids

ORGN 740

Evan A. Hecker, ehecker@mail.utexas.edu and Philip D. Magnus. Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0165
Chartelline C is a member of a small group of highly halogenated indole–imidazole marine alkaloids. Its unique structure includes a 10-membered ring condensed with a unique spiro β-lactam, a 6-bromoindoline and a gem-dimethyl imidazole ring. The securine and securamine alkaloids are believed to be biogenetically related to the chartellines via oxidation pathways. It is anticipated that formation of the spiro β-lactam at a late stage could proceed from a suitable macrolactam via oxidative cyclization. Our work in this area will be presented.