197 1-Benzoxocanes Via Intramolecular Buchwald-Hartwig Etherification

Tuesday, June 30, 2009: 3:30 PM
131 (Morken)
James R. Vyvyan , Department of Chemistry, Western Washington University, Bellingham, WA
Scott L. Bray , Department of Chemistry, Western Washington University, Bellingham, WA
Erik W. Wold , Department of Chemistry, Western Washington University, Bellingham, WA
Courtney A. Engles , Department of Chemistry, Western Washington University, Bellingham, WA

The 1-benzoxocane skeleton, present in the helianane natural products, presents a significant synthetic challenge. Intramolecular hydrosilylation of 2-methyl-5-heptyn-2-ol using Trost's conditions produces cyclic vinyl silane 1. Palladium-catalyzed coupling of 1 with aryl iodides proceeds in high yields to produce tertiary alcohols 2 that contain a Z-olefin. The presence of the olefin facilitates an intramolecular Buchwald-Hartwig etherification reaction to produce the 1-benzoxocane skeleton 3.  Hydrogenation of the olefin produced helianane.  Effects of different R groups, bases, and ligands on the cyclization will be presented.   

                                         

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