Chemistry Letters p. 355 - 358 (1981)
Update date:2022-08-11
Topics:
Sakai, Kazuya
Ohtsuka, Toshikazu
Misumi, Shunjiro
Shirahama, Haruhisa
Matsumoto, Takeshi
Humulene furnished 4,7-epoxy-3-methylene-7,10,10-trimethyl-11-bicyclo<6,3,0>undecanol 9 in 34percent yield employing oxymercuration as a key step.On treatment with BF3.OEt2, 7,11-dihydroxy-3,7,10,10-tetramethyl-3-bicyclo<6.3.0>undecene, which was derived from 9 by ether cleavage, afforded 10α-hydroxy-pentalenene 13 (20percent) along with four byproducts.Oxidation of allylic methyl group of 13 gave methyl pentalenate in 13percent yield from 9.
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