Strategies for the synthesis of 1-benzoxocanes via Caryl—O bond formation

ORGN 355

James R. Vyvyan, vyvyan@chem.wwu.edu and Scott L. Bray, scottlbray@yahoo.com. Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225-9150
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 moderate yields to produce tertiary alcohols 2 that contain a Z-olefin. The presence of the olefin should facilitate an intramolecular Buchwald-Hartwig etherification reaction of 2 to produce the helianane skeleton. Current results will be presented.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008