Flexible Total Synthesis of 11-Deoxylandomycins and Their Non-Natural Analogues by Way of Asymmetric Metal Catalysis
Juyeol Lee
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorJihun Kang
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorSukhyun Lee
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorCorresponding Author
Prof. Young Ho Rhee
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorJuyeol Lee
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorJihun Kang
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorSukhyun Lee
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorCorresponding Author
Prof. Young Ho Rhee
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673 Republic of Korea
Search for more papers by this authorGraphical Abstract
A collective total synthesis of 11- deoxylandomycins is reported using Pd-catalyzed asymmetric hydroalkoxylation of alkoxyallene as the key strategy. This de novo approach allowed for an access to various natural and non-natural congeners of 11-deoxylandomycins.
Abstract
A de novo first collective total synthesis of 11-deoxylandomycins is reported. A signature step is featured by the Pd-catalyzed asymmetric addition of alcohol to ene-alkoxyallenes that assembles oligomeric 2,3,6-trideoxyoligosaccharides. The unique feature of the protocol is illustrated by a flexible access to various natural 11-deoxylandomycins as well as non-natural analogues.
Supporting Information
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