95 γ-ハロエステルの位置選択的開裂反応とその天然物合成への応用(ポスター発表の部)

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Although development of the chemistry of samarium(II) iodide has been of continuing interest in organic synthesis, little attention has focused on the fragmentation reaction. During the course of our studies directed toward the synthesis of physiologically active natural products utilizing the cyclopentane derivative 1, readily accessible from a monoterpene, carvone, as a chiral starting material, we desired to develop an efficient method for the reductive carbon-carbon bond cleavage reaction regioselectively at the β-position to the ester function. The γ-bromo ester 9, prepared from the cyclopentane 8 by addition of hydrogen bromide in acetic acid, was treated with 3 equimolar amounts of samarium(II) iodide in THE and HMPA (20: 1, v/v) at ambient temperature to afford the desired olefin 10 in 48% yield. Reaction of the γ-chloro compound 12, derived from 8 by treatment with hydrogen chloride in ether, with samarium(II) iodide under the same reaction condition as above provided 10 in 77% yield. Treatment of other various y-halo carbonyl compounds with samarium(II) iodide gave the corresponding fragmentation products. The fragmentation reaction developed above was applied to the enantiospecific syntheses of (+)-eldanolide, a sex attractant pheromone, (-)-cis-whisky lactone known as one of the important flavors of whisky, brandy, and so on, and (-)-oudemansin A isolated from mycerial cultures of Oudemansiella mucida.
天然有機化合物討論会の論文
1992-09-10

95 γ-ハロエステルの位置選択的開裂反応とその天然物合成への応用(ポスター発表の部)

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