Microwave assisted and copper(I)-thiophene-2-carboxylate mediated synthesis of azalamellarins

ORGN 424

Carson J. Bruns, brunca01@luther.edu, Department of Chemistry, Luther College, 700 College Drive, Decorah, IA 52101 and Nopporn Thasana, nopporn@tubtim.cri.or.th, Chulabhorn Research Institute, Laboratory of Medicinal Chemistry, Vipavadee-Rangsit Highway, Laksi, Bangkok, 10210, Thailand.
The synthesis of protected azalamellarins L and c is reported using microwave assisted heating techniques as well as copper(I)-mediated Caryl-Namide coupling in the lactamization of the protected azalamellarin precursor. The methodology used afforded protected azalamellarins in 12 steps with an overall yield of 3.8%. The final three steps, those that utilize microwave heating and copper(I) mediation, had yields from 33% to 76% under unoptimized conditions.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008