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Tuesday, August 25 • 2:00pm - 2:40pm
[0013] Synthesis of Natural Products Containing Spiroketals

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Limited Capacity seats available

Natural products have long been regarded as “Nature’s medicine chest” providing invaluable platforms for developing front-line drugs. The chemical structures of natural products have evolved over several millennia for a specific biochemical purpose and their molecular frameworks can be considered “privileged scaffolds.” This lecture will showcase how natural products that contain intricate spiroketal scaffolds can be synthesized thus providing a platform to develop novel anticancer and anti-obesity agents.

The virgatolides are a family of natural products containing a rare benzannulated 6,6-spiroketal moiety isolated in 2011 from Pestalotiopsis virgatula.1 Virgatolides A-C exhibit cytotoxicity against HeLa cells (IC50 ~ 20 µM). The first synthesis2 of virgatolide B is described. Phorbaketal A and alotaketal A are two pseudoenantiomeric natural products, containing a unique spiro-sesterterpenoid core structure.3,4 Phorbaketal A possesses moderate cytotoxicity against a range of cancer cell lines, as well as exhibiting osteoblast and mast cell differentiation activity and inhibition of fatty acid synthesis in the liver. Additionally, alotaketal A activates the cAMP signalling pathway at nanomolar concentrations. Our efforts directed towards the enantioselective syntheses of phorbaketal A and alotaketal A will be described.5

Invited Lecturers
avatar for Margaret Brimble

Margaret Brimble

Distinguished Professor School of Chemical Sciences, University of Auckland
Academic Qualifications | 1983 to 1985 | PhD in Chemistry, The University of Southampton, UK | | 1982 to 1983 | MSc in Chemistry with First Class Honours, The University of Auckland, NZ | | 1979 to 1981 | BSc in Chemistry, The University of Auckland, NZ

Tuesday August 25, 2015 2:00pm - 2:40pm
UCEN Flying A