ISHC2015 has ended

For Campus Prearrival Information <click here>
For a PDF of the 2015 Program Materials <click here>
For ALL Abstracts [1-220] in sequential order <click here>
For ALL Authors of the Lecture and Poster Presentations <click here>

View analytic
Thursday, August 27 • 2:00pm - 2:40pm
[0193] Total Synthesis and Stereochemistry of (+)-Dragmacidin D

Sign up or log in to save this to your schedule and see who's attending!

Limited Capacity seats available

Dragmacidin D is a complex deep-sea marine heterocyclic natural product whose stereochemical identity has remained unclear since its isolation. This bis(indole) pyrazinone alkaloid contains a single stereocenter, whose configuration was proposed based on stereochemistry of another congener, dragmacidin F. Recently, Capon and Jia revised the assignment to 6’’’R based on total synthesis, the first enantioselective preparation of dragmacidin D in 26 steps. We developed an effective direct asymmetric alkylation of arylacetic acids, which enabled the synthesis of (+)-dragmacidin D in 10 steps. Curiously, our own effort confirmed the originally proposed assignment as 6’’’S. We also determined that dragmacidin D undergoes a slow racemization in aqueous solution at pH 6.8, essentially complete within 16 days at room temperature.

Invited Lecturers
avatar for Armen Zakarian

Armen Zakarian

Professor of Chemistry, University of California, Santa Barbara
Armen Zakarian grew up in Moscow, where his scientific interests in chemistry were seeded by a rare opportunity to participate in a research group at the Zelinski Institute of Organic Chemistry during high school and later as an undergraduate student at Moscow State University. The... Read More →

Thursday August 27, 2015 2:00pm - 2:40pm
Corwin West