Acid-Promoted Rearrangement of Drimane Type Epoxy Compounds and Their Application in Natural Product Synthesis
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概要
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The reactions of (±)-α-epoxy drimenol (4) and (±)-α-epoxy drimenyl cyanide (6) with acids (proton acid or Lewis acid) selectively gave the rearranged aldehyde (±)-13 and (±)-15 having the hydroindane skeleton, respectively, while the reactions of (±)-4 and (±)-6 with Dibal-H selectively afforded the allyl alcohol (±)-14 and (±)-16, respectively. The reactions of (8aR)-6 and (8aS)-6 with Dibal-H were applied for the determination of the absolute structure of natural 7β-acetoxy-ent-labda-8(17),13(14)E-dien-15-ol (18). The reaction of (±)-α-epoxy bicyclofarnesol (5) and (8aS)-5 with proton acid selectively provided the rearranged ketol (±)- and (8aS)-31 having the hydroindane skeleton, respectively. The optically active (8aS)-31 was converted to the natural (9S)-austrodoric acid (33).
著者
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Kato Keisuke
Faculty of Pharmaceutical Sciences, Toho University
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Akita Hiroyuki
Faculty Of Pharmaceutical Sciences Toho University
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KINOSHITA Masako
Faculty of Pharmaceutical Sciences, Toho University
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Kato Keisuke
Faculty Of Pharmaceutical Sciences Toho University
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Uchida Akira
Faculty Of Engineering Yamagata University
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Ono Machiko
School Of Pharmaceutical Sciences International Univ. Of Health And Welfare
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Fujiwara Naoko
School of Pharmaceutical Sciences, International University of Health and Welfare
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