Accessing cyclopentachromenes in a single step – UROP Symposium

Accessing cyclopentachromenes in a single step

Nicolas Hernandez

Pronouns:

Research Mentor(s): Corinna Schindler
Research Mentor School/College/Department: Chemistry / LSA
Program:
Authors: Nicolas Hernandez, Emily Traficante, Corinna Schindler
Session: Session 2: 10:00 am – 10:50 am
Poster: 10

Abstract

The optimization of a one-step reaction to access a wide scope of cyclopentachromenes is in progress to elucidate the mechanism and to improve the conditions needed. The intramolecular cyclization of a modified chromanone with a beta alkene tail yields the tricyclic product in high yields. Mechanistically, the reaction most likely proceeds through an alkyne formation from elimination of a vinyl triflate followed by an ene reaction. This research encompasses varying amounts of bases and additives used and reaction time, temperature, and conditions. The reaction scope will also be analyzed to determine how different substituting groups, both on the modified chromanone aryl ring and the alkene, will change the yield of desired product. Upon completion of this method, chemists will have facile access to numerous natural products such as applanatumols X and Y as well as nyingchinoid B, which has certain enzyme inhibiting properties.

Interdisciplinary, Natural/Life Sciences

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