J. Am. Chem. Soc., 129 (42), 12682 -12683, 2007. 10.1021/ja0762339 S0002-7863(07)06233-6
Web Release Date: September 29, 2007

Copyright © 2007 American Chemical Society

Rapid Access to Polyprenylated Phloroglucinols via Alkylative Dearomatization-Annulation: Total Synthesis of (±)-Clusianone1

Ji Qi and John A. Porco, Jr.*

Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215

porco@bu.edu

Received August 18, 2007

Abstract:

A concise approach to the bicyclo[3.3.1]nonane framework of the polyprenylated phloroglucinol natural products utilizing a tandem alkylative dearomatization-annulation sequence is described. Syntheses of (±)-clusianone and a complex adamantane framework have been achieved using the developed methodology.


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