Samroiyotmycins - an Interdisciplinary study of a novel anti-malarial drug

• Main Author: See, Anders Yang Feng
• Other Authors: Roderick Wayland Bates
• Format: Thesis-Doctor of Philosophy
• Language: English
• Published: Nanyang Technological University 2020
• Subjects: Science::Chemistry::Organic chemistry
• Online Access: https://hdl.handle.net/10356/141635
• Institution: Nanyang Technological University

Samroiyotmycins A and B are closely related complex dimeric macrocycles containing 2-unsubstituted oxazole units. Furthermore, biological studies showed that they had anti-malarial activity and were active against a multi-drug resistant strain of Plasmodium falciparum. Hence, they are lead compounds for further investigation to both improve activity and determine if their activity towards the parasite is novel. To our knowledge, there has been no reports of both molecules synthesised in the literature since their isolation and synthesis is the only way to obtain sufficient samples for further studies given its scarcity from natural sources. Herein, a synthetic route to the Samroiyotmycins was devised, successfully furnishing the 2-unsubstituted oxazole moiety using a novel and highly regioselective gold-catalysed 5-exo-dig cyclisation of alkynamides.