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Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies towards (+)-Cortistatin A

Wang, Zhang

The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A.

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More About This Work

Academic Units
Chemistry
Thesis Advisors
Danishefsky, Samuel J.
Degree
Ph.D., Columbia University
Published Here
August 22, 2011