Synthesis of (R)-(-)-3-Methoxymethyl-3-propyl-3,4-dihydrocoumarin from a Chiral Michael Adduct : Absolute Configurations of the Allylated Products of Enantioselective Radical-Mediated Reactions

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概要

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• (R)-3-Methoxymethyl-3-propyl-3,4-dihydrocoumarin was synthesized, starting from a chiral Michael adduct [(S)-methyl 2,3-dihydro-1-oxo-2-(3-oxobutyl)-1H-indene-2-carboxylate], in order to determine the absolute configurations of the products obtained by enantioselective radical-mediated allylation. Aldol cyclization of the Michael adduct proceeded smoothly with suppression of the retro Michael reaction to afford an optically active cyclized product. The Baeyer-Villiger reaction of (R)-2-methoxymethyl-2-propylindanone in the presence of BF_3・Et_2O afforded the desired dihydrocoumarin.

• 公益社団法人日本薬学会の論文
• 1999-10-15

著者

• Yamaguchi H

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• HOSHINO OSAMU

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• Hoshino O

  Sci. Univ. Tokyo Chiba Jpn

• Hoshino Osamu

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• MURAKATA Masatoshi

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• MIZUNO Yusuke

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• YAMAGUCHI Hiromi

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• Mizuno Yusuke

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• Yamaguchi H

  Faculty Of Science Okayama University Of Science

• Murakata M

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• Yamaguchi Hiromi

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

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