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Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes, and application in polyene synthesis

DOI: 10.1021/acs.joc.9b01664 DOI Help

Authors: Haraldur G. Gudmundsson (University of Oxford) , Christian J. Kuper (University of Oxford) , Damien Cornut (University of Oxford) , Felix Urbitsch (University of Oxford) , Bryony L. Elbert (University of Oxford) , Edward A. Anderson (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: The Journal Of Organic Chemistry

State: Published (Approved)
Published: October 2019

Abstract: Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semi-hydrogenation / debenzylation / cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes, and application to a concise total synthesis of leukotriene B3.

Subject Areas: Chemistry


Technical Areas: