Synthesis of 11,14-diacetoxy-13-(acetoxymethyl)podocarpa-8,11,13-triene. Correction of proposed structure for premnolal.

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概要

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• Oxidation of 11-acetoxyabieta-8,11,13-triene, derived from methyl 11-methoxyabieta-8,11,13-trien-18-oate, with chromium trioxide afforded 11,15-diacetoxyabieta-8,11,13-trien-7-one and 11-acetoxy-13-acetylpodocarpa-8,11,13-trien-7-one (<B>11</B>) in a ratio of <I>ca.</I> 2 : 1. The acetyl compound <B>11</B> was converted into a quinone, 13-(hydroxymethyl)podocarpa-8,12-diene-11,14-dione (<B>18</B>), by a series of reactions : iodoform reaction, esterification, acetylation, sodium borohydride reduction, dehydration, catalytic hydrogenation, lithium aluminium hydride reduction, and oxidation with Fremy's salt. Reductive acetylation of <B>18</B> produced 11,14-diacetoxy-13-(acetoxymethyl)-podocarpa-8,11,13-triene (<B>2</B>). The <SUP>1</SUP>H NMR spectrum of <B>2</B> was different from that of 15-acetoxypremnol diacetate which was prepared from natural premnolal. Based on this fact a corrected structure of premnolal is proposed.

• 公益社団法人 日本化学会の論文

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

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