Synthesis of benzoxocane-containing natural products: Heliannuol A, K, and helianane

ORGN 127

James R. Vyvyan, Steven T. Staben, Ryan E. Looper, and Celeste Loitz. Department of Chemistry, Western Washington University, Bellingham, WA 98225
Tin (II) chloride with anhydrous HCl in methylene chloride has been found to efficiently catalyze the regioselective 8-endo cyclization of phenol epoxides 1 to benzoxocanes 2. Both the SnCl2 and HCl are required for optimal production of the benzoxocane. Application of this methodology to the total synthesis of heliannuol A, heliannuol K, and helianane will be presented.

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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004