Efforts towards the synthesis of furan containing bioactive compounds
Abstract
Furan is a valuable subunit in pharmaceutical chemistry. However, there are still
challenges in synthesizing furan-containing compounds. Two approaches have been
attempted to address this issue. 1. Using enynal molecules as a carbene precursor for
synthesizing functionalized furyl-pyrrolidines. A cascade approach was developed for
synthesizing functionalized (2-furyl)-2-pyrrolidines, showcasing both convergence and
remarkable stereoselectivity. This domino process proceeds through an N–H insertion
into enynal-derived metal-carbenoid, followed by an intramolecular aldol reaction to
provide pyrrolidines with high diastereoselectivity (>98:2). This chemistry utilizes Earthabundant zinc chloride as a catalyst with loading as low as 1 mol%. This method operates
under mild conditions and demonstrates high chemoselectivity by accommodating
substrates bearing functionalities such as free alcohols, alkenes, and alkynes. 2 Towards
the total synthesis of collybolide. Collybolide is a natural product that was first isolated
from the fungus Collybia maculata. It has attracted attention due to its potential
therapeutic applications, particularly in the treatment of pain and inflammation. Its
complex structure, however, makes it a challenging target for total synthesis. Our route
starts from simple glutamic acid. This route aimed to minimize the use of chiral reagents
and catalysts to install all 6 stereocenters in Collybolide. So far, after 11 reactions, we
have achieved the intermediate having 15 out of 22 carbon atoms and 4 out of 6
stereocenters in Collybolide without using any chiral reagents and catalysts other than
glutamic acid. One of the significances of this route is that different from the traditional
synthetic route, we installed furan moiety at a very early stage. Furan is known for its
instability, however, in our route, it is stable throughout the synthetic pathway.
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