Collins oxidation of methyl (+)-13.BETA.-abiet-8-en-18-oate and absolute configuration of suaveolic acid.

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概要

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• The oxidation of methyl (+)-13β-abiet-8-en-18-oate with Collins reagent yielded nine oxidation products. Their structures were elucidated on the basis of spectroscopic and chemical data to be methyl (－)-14-hydroxy-7-oxoabieta-8,11,13-trien-18-oate (1% yield), methyl (－)-11,14-dioxoabieta-8,12-dien-18-oate (1%), methyl (+)-11-oxo-13β-abiet-8-en-18-oate (18%), methyl (－)-8α,9α-epoxy-7-oxo-13β-abietan-18-oate (2%), methyl (+)-7-oxoabieta-8,11,13-trien-18-oate (2%), methyl (+)-11,14-dihydroxy-7-oxoabieta-8,11,13-trien-18-oate (2%), methyl (+)-7,11-dioxo-13β-abiet-8-en-18-oate (17%), methyl (+)-14-oxo-13β-abiet-8-en-18-oate (<B>15</B>) (4%), and methyl (+)-7-oxo-13β-abiet-8-en-18-oate (23%) respectively. It is noteworthy that oxygenation occurs not only at the C-7 and C-11 positions but also at the C-14 position. The oxygenated products obtained in this studies could be useful intermediates for the synthesis of the oxidized diterpenoids of abietane skeleton. To exemplify this, <B>15</B> was converted to methyl suaveolate and suaveolol. Hydrolysis of the former yielded suaveolic acid, thus confirming its absolute configuration to be 4R, 5R, 10S, 13S, and 14S.

著者

• Imai Sachihiko

  Department of Chemistry, Faculty of Science, Hiroshima University

• Yuki Shuhei

  Department of Chemistry, Faculty of Science, Hiroshima University

• Matsumoto Takashi

  Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima

• Furutani Manabu

  Department of Chemistry, Faculty of Science, Hiroshima University

• Katayama Arata

  Department of Chemistry, Faculty of Science, Hiroshima University

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