Catalytic, asymmetric synthesis of β-lactams and applications towards the synthesis of pharmacologically active targets

ORGN 668

Meha Shah, and T. Lectka. Department of Chemistry, Johns Hopkins University, 3400 N. Charles St., Chemistry Dept. Remsen Hall, Baltimore, MD 21218
We have developed the catalytic, asymmetric synthesis of monocyclic β-lactams from ketenes and imino esters, utilizing a bifunctional catalyst system. The bifunctional catalyst system employs a chiral nucleophile paired with a Lewis acid to enhance the reactivity of our substrates. Our methodology effectively produces the β-lactam core with a variety of substituents in excellent yield with high enantio- and diastereoselectivity. The β-lactam core is of keen interest to the pharmaceutical industry due its presence in many pharmacologically active drugs. We have applied our methodology to the synthesis of three interesting targets, namely, an effective PSA inhibitor, a penicillin derivative, and a nocardicin.


Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005