Progress towards the total synthesis of citrinadin A.
Our efforts in the Wood laboratories focus on the synthesis of structurally intriguing and challenging natural products with promising biological activity. Recently, our attention turned to Kobayashi’s report of citrinadin A (1), an alkaloid isolated from a marine fungus with a unique pentacyclic core. This compound exhibits cytotoxicity against murine leukemia and human epidermoid carcinoma cells.
The reported structure of this compound details an N,N-dimethyl-L-valine derivative on the quinolizidine ring system and an a,b-epoxy carbonyl unit at the C(7) oxindolic position. We plan to employ free radical conditions to construct the core spiro-oxindole in a tandem cyclization sequence. We hope to then explore conditions for coupling this eastern half of the natural product with an appropriately substituted piperidine in a convergent manner.
Name: Elnaz Menhaji
Age: 26
Birthday: September 21, 1980
Graduate Level: 5th year
Undergrad: Barnard College
Degree: B.A. Biochemistry
Graduate: Yale University
Degree: M.S. Chemistry
Hobbies: Dancing, running, and cooking.
E-mail: elnaz.menhaji@yale.edu
