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Communication | Regular issue | Vol 38, No. 7, 1994, pp.1491-1496
Published online, 1st January, 1970
DOI: 10.3987/COM-94-9754
Lewis Acid Promoted Tandem [4+2] Cycloaddition-Rearrangement Process — A Simple and Efficient Synthesis of Highly Functionalized Oxabicyclo[3.3.1]nonanes

Masahiro Toyota, Yoshihiro Wada, Youichi Nishikawa, Toshihiro Wada, and Keiichiro Fukumoto*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Catalytic Lewis acid promoted tandem [4+2]cycloaddition-rearrangement processes of the trienic esters (4), (8) and (9) are reported. The novel tandem reactions proceed under thermal (110 °C, aluminum catalyst) conditions and afford the highly functionalized oxabicycl[3.3.1]nonanes (5), (10) and (11), respectively.