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Jozef Stec

Jozef Stec

Marshall B. Ketchum University, USA

Title: Transition metal-assisted total synthesis of natural products

Biography

Jozef Stec is currently an Associate Professor of Medicinal Chemistry at Marshall B. Ketchum University College of Pharmacy. He obtained MSc (Honors) in Molecular and Pharmaceutical Biotechnology (Gdansk University of Technology); PhD in Organic and Organometallic Chemistry (University of Southampton), and Post-doctoral training in Synthetic Medicinal Chemistry (University of Illinois at Chicago). His research interest is in the area of widely understood synthetic organic and modern medicinal chemistry. His research productivity is documented by manuscripts published in reputed international journals. He is also involved in teaching and numerous professional service activities.

Abstract

Chemical transformations mediated by transition metals play pivotal role in modern organic chemistry. New reaction development and total synthesis of complex natural products are only a few examples of harnessing the organometallic chemistry. Organozirconium chemistry was successfully utilized in the total synthesis of natural products as exemplified by the recently reported total synthesis of (+)-mucosin. The developed methodology utilized the one-pot two-step zirconocene-mediated co-cyclisation of triene followed by insertion of silylcarbenoid generated in situ, to give the expanded zirconacycle. Protonolysis of zirconacycle followed by the modified Flaming-Tamao oxidation gave the bicyclic alcohol which was oxidized to its corresponding aldehyde by using the Swern protocol. Takaiolefination provided the protected alcohol which was converted to the corresponding carboxylic acid via TBAF deprotection and PDC oxidation. Esterification using diazomethane procedure gave the methyl ester of (+)-mucosin, which is the dextrorotatory enantiomer of the naturally isolated ( )-mucosin methyl ester.