Issue 40, 2019, Issue in Progress
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RSC Advances

Total synthesis of the plant alkaloid racemic microthecaline A: first example of a natural product bearing a tricyclic quinoline-serrulatane scaffold

Thirupathi Reddy Penjarla,ab   Maheshwar Kundarapu,b   Syed Mohd. Baquerb  and  Anupam Bhattacharya ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Birla Institute of Technology and Science-Pilani (Hyderabad Campus), Hyderabad-500078, India
E-mail: anupam@hyderabad.bits-pilani.ac.in
Fax: +91-40-66303998
Tel: +91-40-66303522

b Department of Medicinal Chemistry, GVK Biosciences Pvt. Ltd., Survey No. 125 (Part) & 126, IDA Mallapur, Hyderabad 500076, India

Abstract

The first total synthesis of racemic microthecaline A, a quinoline serrulatane alkaloid, isolated from the Australian desert plant Eremophila microtheca is described. The natural product was synthesized in ten steps, starting from ethyl 4-bromo-6-methoxy-8-methylquinoline-3-carboxylate in 8% overall yield.

Graphical abstract: Total synthesis of the plant alkaloid racemic microthecaline A: first example of a natural product bearing a tricyclic quinoline-serrulatane scaffold

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Article information

DOI
https://doi.org/10.1039/C9RA04675E
Article type
Paper
Submitted
22 Jun 2019
Accepted
22 Jul 2019
First published
26 Jul 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 23289-23294

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Total synthesis of the plant alkaloid racemic microthecaline A: first example of a natural product bearing a tricyclic quinoline-serrulatane scaffold

T. R. Penjarla, M. Kundarapu, S. Mohd. Baquer and A. Bhattacharya, RSC Adv., 2019, 9, 23289 DOI: 10.1039/C9RA04675E

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