Rotational spectrum and carbon atom structure of dihydroartemisinic acid

Pate, Brooks

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https://hdl.handle.net/2142/91447 Copy

Description

Title

Rotational spectrum and carbon atom structure of dihydroartemisinic acid

Author(s)

Pate, Brooks

Contributor(s)

• Spada, Lorenzo
• Seifert, Nathan A.
• Evangelisti, Luca

Issue Date

2016-06-22

Keyword(s)

Spectroscopy as an analytical tool

Abstract

Dihydroartemisinic acid (DHAA, C$_{15}$H$_{24}$O$_{2}$, five chiral centers) is a precursor in proposed low-cost synthetic routes to the antimalarial drug artemisinin. In one reaction process being considered in pharmaceutical production, DHAA is formed from an enantiopure sample of artemisinic acid through hydrogenation of the alkene. This reaction needs to properly set the stereochemistry of the asymmetric carbon for the synthesis to produce artemisinin. A recrystallization process can purify the diastereomer mixture of the hydrogenation reaction if the unwanted epimer is produced in less than 10\% abundance. There is a need in the process analytical chemistry to rapidly (less than 1 min) measure the diastereomer excess and current solutions, such a HPLC, lack the needed measurement speed. The rotational spectrum of DHAA has been measured at 300:1 signal-to-noise ratio in a chirped-pulsed Fourier transform microwave spectrometer operating from 2-8 GHz using simple heating of the compound. The $^{13}$C isotope analysis provides a carbon atom structure that confirms the diastereomer. This structure is in excellent agreement with quantum chemistry calculations at the B2PLYPD3/ 6-311++G level of theory. The DHAA spectrum is expected to be fully resolved from the unwanted diastereomer raising the potential for fast diastereomer excess measurement by rotational spectroscopy in the pharmaceutical production process.

Publisher

International Symposium on Molecular Spectroscopy

Type of Resource

text

Language

En

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http://hdl.handle.net/2142/91447

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Copyright 2016 by the authors

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