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Note | Regular issue | Vol 45, No. 8, 1997, pp.1573-1578
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7838
First Isolation and Determination of Three Humulene Triepoxides

Kiyoharu Hayano* and Katsura Mochizuki

*Chemistry Laboratory, Hokkaido College of Education, Ainosato, Sapporo, Hokkaido 002-8502, Japan


The epoxidation of (9E)-(2R*, 3R*, 6R*, 7R*)-2,3;6,7-diepoxy-3,7,11,11-tetramethylcycloundec-9-ene (1TC) with m-CPBA gave two triepoxides, (2R*, 3R*, 6R*, 7R*, 9S*, 10S*)- and (2R*, 3R*, 6R*, 7R*, 9R*, 10R*)-2,3;6,7;9,10-triepoxy-3,7,11,11-tetramethylcycloundecane (3 and 4), in the ratio of 3 : 4 = 52 : 48. The epoxidation of (9E)-(2S*, 3S*, 6R*, 7R*)-2,3;6,7-diepoxy-3,7,11,11-tetramethylcycloundec-9-ene (2CT) gave only one triepoxide, (2S*, 3S*, 6R*, 7R*, 9S*, 10S*)-2,3;6,7;9,10-triepoxy-3,7,11,11-tetramethylcycloundecane (5). The configurations for 4 and 5 were determined by X-Ray crystallogrphy.