Total Syntheses of Naturally Occurring Opium Alkaloid, Codeine and Indolosesquiterpene Alkaloid, Xiamycins

Mondal, Ayan (2024) Total Syntheses of Naturally Occurring Opium Alkaloid, Codeine and Indolosesquiterpene Alkaloid, Xiamycins. PhD thesis, Indian Institute of Science Education and Research Kolkata.

Text (PhD thesis of Ayan Mondal (19RS040)) 19RS040.pdf - Submitted Version Restricted to Repository staff only Download (29MB)

Abstract

Codeine (1) is a naturally occurring opiate and prodrug of morphine and mainly used to treat acute pain, coughing, and diarrhea. It is found naturally in the sap of the opium poppy, Papaver somniferum. Codeine (1) is marketed as both a single-ingredient drug and in combination preparations with paracetamol. It is on the World Health Organization's list of essential medicines. On the other hand, indolosesquiterpene alkaloids are composed of an architecturally intriguing pentacyclic framework with four contiguous stereo genic centres with carbazole unit. In 2010, xiamycin A (2) and xiamycin A methyl ester, displaying anti-HIV and antibiotic activities, were isolated by Hertweck et. al. from Streptomyces sp. GT2002/15032a and HKI0595, endophytes from the mangrove plant Bruguiera. As a part of my PhD program and in connection with the alkaloid total synthesis, we targeted for the total synthesis of opium alkaloid, codeine and indolosesquiterpene alkaloids, such as xiamycin A. In this seminar, asymmetric strategies to these natural products, in particular utilizing transition-metal catalyzed key processes will be discussed.

Actions (login required)

View Item