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Communication | Regular issue | Vol 48, No. 9, 1998, pp.1747-1752
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8240
Epoxidation of Four Possible Conformers of Humulene 9,10-Epoxide: First Isolation of 2R*, 3R*, 6S*, 7S*, 9S*, 10S*-Humulene 2,3;6,7;9,10-Triepoxide

Kiyoharu Hayano,* Nobue Ito, Makoto Sato, Masayuki Takishima, and Katsura Mochizuki

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


The complete reaction of humulene 9,10-epoxide {(2E, 6E)-9,10-epoxy-3,7,11,11-tetramethylcycloundeca-2,6-diene, (1)} with m-CPBA produced a hitherto unknown 2R*, 3R*, 6S*, 7S*, 9S*, 10S*-2,3;6,7;9,10-triepoxy-3,7,11,11-tetramethylcycloundecane (6) together with three known humulene triepoxides (7, 8 and 9), in the ratio of 6 : 7 : 8 : 9 = 1.3 :11.5 : 22.6 : 64.6. The configuration of 6 was determined X-Ray crystallography (C15H24O3: space group p21/n with a = 14.147 (4) Å, b = 8.419 (3) Å, c = 12.238 (4) Å, β = 102.10 (3)°, Z = 4). The new triepoxide (6) maintained configuration corresponding to the TT conformer, one of the four possible conformers of 1.